Oxime derivatives and agricultural chemicals containing the same

ABSTRACT

Various oxime derivatives are provided, which do not cause any chemical damage to plants and which exhibit sufficient effectiveness against various plant diseases. The oxime derivatives are expressed by two general chemical formulas (1) and (2), as follows.                    
     Agricultural chemicals and plant disease control chemicals are also provided which contain the above mentioned oxime derivatives as active ingredients. Test results of these agricultural chemicals and the plant disease control chemicals are proved to be very effective for downey mildews and late blights or Phytophthora rot etc.

TECHNICAL FIELD

This invention relates to novel oxime derivatives and agriculturalchemicals including the oxime derivatives as active ingredients and,particularly relates to control chemicals for plant diseases.

BACKGROUND ART

Regarding oxime derivatives which are effective as agriculturalchemicals or pesticides, Japanese Patent Application, First PublicationNo. Hei 7-25224 by the present inventors discloses, for example, that 4,5-substituted-1, 2, 3-thiadiazole derivatives are effective as controlchemicals for plant diseases.

Although the above derivatives are effective as control chemicals, it isdesired to develop new agricultural chemicals which are superior ineffects in a lesser amount than the above thiadiazole derivatives.

DISCLOSURE OF INVENTION

The problems to be solved by the present invention are, therefore, toprovide a new oxime derivative which is sufficiently effective to treatplant diseases in small amounts without causing damage or phytotoxicityto the plant and agricultural chemicals or pesticides containing theabove mentioned oxime derivative as an active ingredients, particularly,as the control chemicals for plant diseases.

The inventors of the present invention have synthesized new oximederivatives and have investigated bioactivities of these derivatives inorder to solve the above problems. After a series of investigations,this invention was completed by discovering that oxime derivativesrepresented by general chemical formulas (1) and (2) are particularlyeffective, showing superior bioactivity against various bacteria causingplant diseases, and without showing any phytotoxicity.

The present invention provides the following oxime derivatives andagricultural chemicals containing said oxime derivatives as effectiveagents:

(1) an oxime derivative represented by the following general chemicalformula (1),

 wherein,

R¹ represents a hydrogen atom or a lower alkyl group; X represents ahalogen atom, a nitro group, a hydroxyl group, a cyano group, a carboxylgroup, an alkoxy-carbonyl group, a lower alkyl group which may besubstituted with halogen atoms; a lower alkoxy group which may besubstituted with halogen atoms; a lower alkylthio group which may besubstituted with halogen atoms; a lower alkylsulfonyl group which may besubstituted with a halogen atom; an aryl group which may be substitutedwith a halogen atom or a lower alkyl group; an aryloxy group which maybe substituted with a halogen atom or a lower alkyl group; or an aminogroup which may be substituted with a lower alkyl group; and nrepresents an integer from 0 to 3; and

Het A represents a 6-membered aromatic nitrogen-containing ring whichcontains one or two nitrogen atoms or its benzo-condensation ring-typenitrogen containing aromatic ring which may be substituted with one ortwo substitutable groups selected from the group consisting of a halogenatom, a lower alkyl group, a lower alkylthio group, a loweralkylsulfonyl group, a lower alkoxy group, a trifluoromethyl group, anda cyano group; and

Het B represents oxime derivatives, each ring structure, expressed bythe following formulas,

 wherein,

Y represents a hydrogen atom, a halogen atom, or a lower alkyl groupwhich may be substituted with a halogen atom;

(2) an oxime derivative expressed by the following general chemicalformula (2);

 [wherein,

R¹ ,X, n, Het B, and Y are the same as those defined in the chemicalformula (1), and Het C represents a 5-membered nitrogen containingaromatic ring or its benzo-condensation ring-type nitrogen containingaromatic ring which contains more than one nitrogen atom, or which maycontain a sulfur atom or an oxygen atom, and which may be substitutedwith more than one substituting group, and the substitutable groups on anitrogen atom of said 5-membered nitrogen containing aromatic ring aregroups selected from the group consisting of a lower alkyl group, alower alkyl-sulfonyl group, triphenylmethyl group, a lower alkoxymethylgroup and a N, N-di-substituted sulfamoyl group substituted with loweralkyl groups, and the substitutable groups on a carbon atom of said 5membered nitrogen containing aromatic ring are groups selected from thegroup consisting of a halogen atom, a cyano group, an alkyl groupranging from C₁ to C₆ which may be substituted with a halogen atom, anda cycloalkyl group ranging from C₃ to C₆; and

an alkenyl group ranging from C₂ to C₆, an alkinyl group ranging from C₂to C₆, an alkoxy group ranging from C₁ to C₅ which may be substitutedwith a halogen atom, a lower alkylthio group which may be substitutedwith a halogen atom, a lower alkylsulfonyl group which may besubstituted with a halogen atom, a lower alkyl sulfinyl group which maybe substituted with halogen atoms, an amino group which may besubstituted with a lower alkyl group or a cycloalkyl group ranging fromC₃ to C₆ or a triphenyl-methyl group; and

a lower alkoxy-carbonyl group, a carbamoyl group which may besubstituted with lower alkyl groups, an aminomethyl group which may besubstituted with lower alkyl groups, an acylaminomethyl group,N-alkoxycarbonyl-aminomethyl group, an alkyl thiomethyl group, arylgroup which may be substituted with halogen atoms, and a heteroarylgroup which may be substituted with halogen atoms, and

a group expressed by —N (R²) C (═O) R³ (wherein, R² represents ahydrogen atom or a methyl group, and R represents a hydrogen atom, analkyl group ranging from C₁ to C₁₀ which may be substituted with halogenatoms, a cycloalkyl group ranging from C₃ to C₈, an alkenyl groupranging from C₂ to C₆, an alkinyl atoms ranging from C₂ to C₄, anaralkyl group, a lower alkyl group substituted with an amino group, anaralkyl group substituted with an amino group, a lower alkyl groupsubstituted with an acylamino group, an aralkyl group substituted withan acylamino group, a lower alkyl group substituted with analkoxy-carbonyl-amino group, an aralkyl group substituted with analkoxy-carbonyl-amino group, an aryl group which may be substituted withhalogen atoms, lower alkyl groups which may be substituted with halogenatoms, lower alkoxy groups, lower alkylthio groups, amino groups, nitrogroups or cyano groups, a heteroaryl group, a lower alkoxy group, acycloalkyloxy group ranging from C₃ to C₆, a benzyloxy group and anaryloxy group)],

(3) an oxime derivative expressed by the chemical formula (1), whereinHet A is a pyridyl group which may be substituted with one halogen atomor a lower alkyl group;

(4) an oxime derivative expressed by the chemical formula (2), whereinthe Het C is a thiazolyl group which is expressed by the followingchemical formula,

 [wherein,

R⁴ represents a hydrogen atom, an amino group, an alkoxy group rangingfrom C₁ to C₅ which may be substituted with halogen atoms, a loweralkylthio group which may be substituted with halogen atoms, a loweralkylsulfonyl group which may be substituted with halogen atoms, a loweralkylsulfinyl group which may be substituted with halogen atoms; or

a —NHC (═O) R³ group (wherein, R³ represents a hydrogen atom, an alkylgroup ranging from C₁ to C₁₀ which may be substituted with halogenatoms, a cycloalkyl group ranging from C₃ to C₈, an alkenyl groupranging from C₂ to C₆, an alkinyl group ranging from C₂ to C₄, anaralkyl group, a lower alkyl group substituted with an amino group, anaralkyl group substituted with an amino group, a lower alkyl groupsubstituted with an acylamino group, an aralkyl group substituted withan acyl-amino group,

a lower alkyl group substituted with an alkoxycarbonylamino group, anaralkyl group substituted with an alkoxycarbonylamino group; an arylgroup which may be substituted with halogen atoms, lower alkyl groupswhich may be substituted with halogen atoms, lower alkoxy groups, loweralkylthio groups, amino groups, nitro groups, or cyano groups; aheteroaryl group, a lower alkoxy group, or a cycloalkyloxy group rangingfrom C₃ to C₆, a benzyl oxy group, or a aryloxy group); and

R⁵ represents a hydrogen atom, a halogen atom, or a lower alkyl groupwhich may be substituted with a halogen atom];

(5) the oxime derivative recited in the above (4), in which R⁴ is agroup expressed by —NHC (═O) R³ (wherein, R³ represents a hydrogen atom,an alkyl group ranging from C₁to C₆ which may be substituted withhalogen atoms, a lower cycloalkyl group ranging from C₃ to C₆, an arylgroup which may be substituted with halogen atoms, lower alkyl groupswhich may be substituted with halogen atoms, lower alkoxy groups, aminogroups, or cyano groups; a heteroaryl group, or a lower alkoxy group),and R⁵ is a hydrogen atom;

(6) a pesticide which contains at least one of the oxime derivatives ofthe above components recited in (1) to (5) as active ingredient;

(7) a plant disease control agent which contains at least one of theoxime derivatives of the above components recited in (1) to (5) asactive ingredient;

(8) a plant disease control agent as recited in (7), which is effectivefor plant diseases caused by mold fungi.

BEST MODE FOR CARRYING OUT THE INVENTION

In the oxime derivatives expressed by the general chemical formulas (1)and (2), R¹ represents a hydrogen atom or a lower alkyl group. Thestructure of the lower alkyl group may be linear or branched, andexamples of the lower alkyl group include, for example, a methyl group,an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group,an isobutyl group, a sec-butyl group, and a cyclopropyl group, all ofwhich range from C₁to C₄. Particularly preferable groups are a hydrogenatom and a methyl group.

In the general formulas (1) and (2), X represents halogen atoms, a nitrogroup, a hydroxyl group, a cyano group, a carboxyl group, analkoxycarbonyl group, a lower alkyl group which may be substituted withhalogen atoms, a lower alkoxy group which may be substituted withhalogen atoms, an alkylthio group which may be substituted with halogenatoms, a lower alkylsulfonyl group which may be substituted with halogenatoms, an aryl group which may be substituted with halogen atoms orlower alkyl groups, an aryloxy group which may be substituted withhalogen atoms or lower alkyl groups, or an amino group which may besubstituted with lower alkyl groups.

Here, examples of the halogen atoms include a chlorine atom, a bromineatom, a iodine atom, and a fluorine atom; and examples of thealkoxycarbonyl group include a methoxycarbonyl group, a ethoxycarbonylgroup, and a n-propylcarbonyl group; examples of the lower alkyl groupswhich may be substituted with halogen atoms include linear or branchedlower alkyl groups ranging from C₁ to C₄ such as a methyl group, anethyl group, a n-propyl group, an isopropyl group, a n-propyl group, an-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group,lower halogen-substituted alkyl groups such as a chloromethyl group, adifluoromthyl group, a trifluoromethyl group, a difluorochloromethylgroup, a pentafluoroethyl group, 3. 3. 3-trifluoro-n-propyl group.

Examples of lower alkoxy groups which may be substituted with halogenatoms include a methoxy group, an ethoxy group, a n-propoxy group, anisopropoxy group, a n-butoxy group, an isobutoxy group, a sec-butoxygroup, a tert-butoxy group, a cyclopropyloxy group, a difluromethoxygroup; and examples of lower alkylthio groups which may be substitutedwith halogen atoms include a methylthio group, an ethylthio group, an-propylthio group, an isopropylthio group, an n-butylthio group, anisobutylthio group, a sec-butylthio group, a difluoromethylthio group, atrifluoromethylthio group, and a cyclopropylthio group.

Examples of lower alkylsulfonyl groups which may be substituted withhalogen atoms include methanesulfonyl group, a ethanesulfonyl group, an-propanesulfonyl group, an isopropanesulfonyl group, a n-butanesulfonylgroup, a difluoromethanesulfonyl group, and a trifluoromethanesulfonylgroup. Examples of aryl groups which may be substituted with halogenatoms or lower alkyl groups include a phenyl group, a 4-chlorophenylgroup, a 4-tolyl group, and a 3-fluorophenyl group.

Examples of aryloxy groups which may be substituted with halogen atomsor lower alkyl groups include a phenoxy group and a 4-florophenoxygroup; and examples of amino groups which may be substituted with loweralkyl groups include an amino group, a methylamino group, an ethylaminogroup, a n-propylamino group, an isoproylamino group, a n-butylaminogroup, an isobutylamino group, a sec-butylamino group, a tert-butylaminogroup, a dimethylamino group, a diethylamino group, a di-n-propylaminogroup, a di-n-butylamino group, an ethylmethylamino group, amethyl-n-propylamino group, an ethyl-n-propylamino group, anethyl-n-propylamino group, and a cyclopropylamino group.

The substituting position of X is not limited, and n represents aninteger ranging from 0 to 3. When n is 2 or 3, X may be identical ordifferent. Preferable examples of X include a hydrogen atom, a loweralkyl group ranging from C₁to C₃, a fluoroalkyl group ranging from C₁toC₂, and a halogen atom, and the most preferable examples include ahydrogen atom, a trifluoromethyl group, a fluorine atom, and a chlorineatom.

The Het A in the general formula (1) represents a 6-membered nitrogencontaining aromatic ring which contains 1 or 2 nitrogen atoms , or itsbenzo-condensation ring-type nitrogen-containing ring, which may besubstituted with 1 or 2 substituting groups. Examples of the 6-memberednitrogen containing aromatic rings include a pyridine ring, a pyrimidinering, a pyrazine ring, and a pyridazine ring; and examples of thebenzo-condensation ring-type nitrogen containing aromatic rings includea quinoline ring, a quinazoline ring, and a quinoxaline ring.

Examples of substitutable groups on the Het A include a halogen atom, alower alkyl group, a lower alkylthio group, a lower alkylsulfonyl group,a lower alkoxy group, a trifluoromethyl group and a cyano group, and, inmore detail, the halogen atoms may include a chlorine atom, a bromineatom, a fluorine atom; the lower alkyl groups may include linear orbranched lower alkyl groups such as a methyl group, an ethyl group, an-propyl group, an isopropyl group, a n-butyl group, an isobutyl group,and a sec-butyl group; and examples of the lower alkylthio groups arelinear or branched alkylthio groups such as a methylthio group, anethylthio group, a n-propylthio group, an isopropylthio group, an-butylthio goup, an isobutylthio group, and a sec-butylthio group.

Examples of the lower alkylsulfonyl groups include linear or branchedalkylsulfonyl groups such as a methanesulfonyl group, an ethanesulfonylgroup, a propanesulfonyl group, an isopropanesulfonyl group, abutanesulfonyl group, an isobutanesulfonyl group, and asec-butanesulfonyl group; and examples of the lower alkoxy groupsincludes linear or branched lower alkoxy groups such as a methoxy group,an ethoxy group, a n-butoxy group, an isobutoxy group, and a sec-butoxygroup.

A preferable example of the Het A is a pyridin-2-yl group, and the mostpreferable examples of the Het A include a pyridin-2-yl group or a5-methylpyridin-2-yl group.

Het B in the general formulas (1) and (2) is expressed by the followingformulas,

(wherein, Y represents a hydrogen atom, a halogen atom, and a loweralkyl group which may be substituted with a halogen atom), and wherein,Het B represents a 1, 2, 3-thiadiazol-4-yl group, a 1, 2,5-thiadiazol-3-yl group, or 1, 2, 5-oxyadiazol-3-yl group or theirhalogenaged derivatives, or derivatives substituted with a lower alkylgroup which is substituted with a halogen or not substituted.

Examples of the halogen atoms represented by Y include a fluorine atom,a chlorine atom, a bromine atom; and examples of the lower alkyl groupswhich may be substituted with halogen atoms include lower alkyl groupsranging from C₁ to C₄ such as a methyl group, an ethyl group, a n-propylgroup, an isoropyl group, a difluoromethyl group, and a trifluoromethylgroup, and the most preferable group is a methyl group.

Het C in the general formula (2) represents a 5-membered nitrogencontaining aromatic ring or its benzo-condensation nitogen containingaromatic ring, which contains more than one nitrogen atom, which maycontain a sulfur atom or a oxygen atom, and which may be substitutedwith more than one substituting group.

Examples of the 5-membered nitrogen containing aromatic rings include apyrrole ring, a imidazole ring, a oxazole ring, a thiazole ring, apyrazole ring, an isoxazole ring, an isothiazole ring, a 1, 2,3-triazole ring, a 1, 2, 4-triazole ring, a 1, 2, 3-oxadiazole ring, a1, 2, 4-oxadiazole ring, a 1, 2, 5-oxadiazole ring, a 1, 3, 4-oxadiazolering, a 1, 2, 3-thiadiazole ring, a 1, 2, 4 thiadiazole ring, a 1, 3, 4thiadiazole ring, 1, 2, 4 thiadiazole ring and a tetrazole ring; andexamples of its benzo-condensation ring-type nitrogen containingaromatic rings include a benzimidazole ring, a benzoxazole, abenzthiazole, a imidazo [1, 2-a] pyridine ring, a [1, 2, 4] triazo [1,5-a] pyridine ring.

Examples of the groups substitutable on the nitrogen atom of the Het Cgroup include a lower alkyl group, a lower alkylsulfonyl group, atriphenylmethyl group, a lower alkoxymethyl group, and a N,N-di-substituted-sulfamoyl group substituted with lower alkyl groups,wherein examples of the lower alkyl groups include a methyl group, anethyl group, a n-propyl group, an isopropyl group, a n-butyl group, anisobutyl group, and a sec-butyl group; and examples of loweralkylsulfonyl group include a methanesulfonyl group, an ethanesulfonylgroup, a n-propanesulfonyl group, an isopropanesulfonyl group, an-butanesulfonyl group, and an isobutanesulfonyl group; example of loweralkoxymethyl group include a methoxymethyl group and an ethoxymethylgroup; examples of N,N-di-substituted sulfamoyl group substituted withlower alkyl groups include a dimethylsulfamoyl group and adiethylsulfamoyl group.

Examples of groups which are substitutable on the carbon atom of the HetC group include a halogen atom, a cyano group, an alkyl group rangingfrom C₁ to C₆ which may be substituted with halogen atoms, a cycloalkylgroup ranging from C₃ to C₆, an alkenyl group ranging from C₂ to C₆, analkynyl group ranging from C₂ to C₆, an alkoxy group ranging from C₁ toC₅ which may be substituted with halogen atoms, a lower alkylthio groupwhich may be substituted with halogen atoms, a lower alkylsulfonyl groupwhich may be substituted with halogen atoms, a lower alkylsulfinyl groupwhich may be substituted with halogen atoms, and an amino group whichmay be substituted with lower alkyl groups or cycloalkyl groups rangingfrom C₃ to C₆ or triphenylmethyl groups; and

a group expressed by a formula —N (R²) C (═O) R³ (wherein, R² representsa hydrogen atom or a methyl group and R¹ represents a hydrogen atom, analkyl group ranging from C₁ to C₁₀ which may be substituted with halogenatoms, preferably from C₁ to C₈, a cycloalkyl group ranging from C₃ toC₈, preferably from C₃ to C₆, an alkenyl group ranging from C₂ to C₆, anaralkyl group, a lower alkyl group substituted with an amino group, anaralkyl group substituted with an amino group, a lower alkyl groupsubstituted with an acylamino group, an aralkyl group substituted withan acylamino group, a lower alkyl group substituted with analkoxycarbonylamino group, an aralkyl group substituted with analkoxycarbonylamino group; and

a halogen atom, and a lower alkyl group which may be substituted withhalogen atoms, a lower alkoxy group, a lower alkylthio group, an aminogroup, an aryl group which may be substituted with a nitro group or acyano group; a heteroaryl group, a lower alkoxy group, a cycloalkyloxygroup, a benzyloxy group or a aryloxy group); and

a lower alkoxycarbonyl group, a carbamoyl group which may be substitutedwith lower alkyl groups, an aminomethyl group which may be substitutedwith lower alkyl groups, an acylaminomethyl group, aN-alkoxycarbonylaminomethyl group, an alkylthiomethyl group, and an arylgroup or a heteroaryl group which may be substituted with halogen atoms.

More practically, examples of the halogen atoms include a chlorine atom,a fluorine atom, and a bromine atom; examples of the alkyl groups whichmay be substituted with halogen atoms include a methyl group, an ethylgroup, a n-propyl group, an isopropyl group, a n-butyl group, anisobutyl group, a n-hexyl group, a difluoromethyl group, and atrifluoromethyl group; examples of the cycloalkyl groups ranging from C₃to C₆ include a cyclopropyl group, a cyclopentyl group, and a cyclohexylgroup; and examples of the alkenyl groups ranging from C₂ to C₆ includea vinyl group, an allyl group, a butenyl group, and a hexenyl group.

Examples of the alkynyl groups ranging from C₂ to C₆ include a ethynylgroup, a propargyl group, and a butynyl group; and examples of the loweralkoxy groups ranging from C₁to C₅ carbon atoms, which may besubstituted with halogen atoms include a methoxy group, an ethoxy group,a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxygroup, a sec-butoxy group, a n-pentyloxy group, a difluoromethoxy group,and a trifloromethoxy group.

Examples of lower alkylthio groups which may be substituted with halogenatoms include a methylthio group, an ethylthio group, a propylthiogroup, an isopropylthio group, a butylthio group, an isobutylthio group,a sec-butylthio group, a difluoromethylthio group, and atrifluoromethylthio group.

Examples of lower alkylsulfonyl groups which may be substituted withhalogen groups include a methanesufonyl group, an ethanesulfonyl group,a propanesulfonyl group, an isopropanesulfonyl group, a butanesulfonylgroup, a difluoromethanesulfonyl group, and a trifluoromethanesulfonylgroup; and examples of lower alkylsulfinyl groups which may besubstituted with halogen atoms include a difluoromethanesulfinyl groupand a trifluoromethanesulfinyl group.

Examples of the amino groups which may be substituted with lower alkylgroups or cycloalkyl groups ranging from C₃ to C₆ include an aminogroup, a methylamino group, an ethylamino group, a propylamino group, anisopropylamino group, a butylamino group, an isobutylamino group, asec-butylamino group, a dimethylamino group, a diethylamino group, adipropylamino group, a dibutylamino group, an ethylmethylamino group, amethylpropylamino group, anethylpropylamino group, a cyclopropylaminogroup, a cyclopentylamino group, and a cyclohexylamino group.

Examples of the lower alkoxycarbonyl groups include a methoxycarbonylgroup, an ethoxycarbonyl group, and a propoxycarbonyl group; examples ofcarbamoyl groups which may be substituted with lower alkyl groupsinclude a N-methylcarbamoyl group, a N-ethylcarbamoyl group, aN-isopropylcarbamoyl group, and a N, N-diethylcarbamoyl group; andexamples of the aminomethyl group which may be substituted with a loweralkyl groups include an aminomethyl group, a N-methylaminomethyl group,a N-ethylaminomethyl group, a N-propylaminomethyl group, aN-isopropylaminomethyl group, a N-butylaminomethyl group, aN,N-dimethylaminomethyl group, and a N, N-diethylaminomethyl group.

Examples of the acylaminomethyl groups include a formylaminomethylgroup, an acetylaminomethyl group, a propionylaminomethyl group, abutyrylaminomethyl group, an isobutyrylaminomethyl group, abenzoylaminomethyl group, and a N-acetyl-N-isopropylaminomethyl group;examples of the N-alkoxycarbonylaminomethyl groups include amethoxycarbonylaminomethyl group, an ethoxycarbonylaminomethyl group, at-butoxycarbonylaminomethyl group, and aN-(t-butoxycarbonyl)-N-isopropylaminomethyl group; and an example of thealkylthiomethyl group is a isopropylaminomethyl group.

Examples of the aryl groups which may be substituted with halogen atomsinclude a phenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group,a 4-fluorophenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group,a 4-chlorophenyl group, a 2, 4-dichlorophenyl group, a 3,4-dichlorophenyl group, a 2, 6-dichlorophenyl group, a naphthyl group,and a biphenyl group; and examples of the heteroaryl groups include apyridin-2-yl group, a pyridin-4-yl group, a pyridin-3-yl group, a2-furyl group, a 3-furyl group, a 2-thienyl group, a 3-thienyl group, aquinoyl group, a indolyl group, a benzofuranyl group, a benzthienylgroup, a benzthiazolyl group, a benzisoxazolyl group, and abenzisothiazolyl group.

Practical examples of the R³ in the —N (R²) C (═O) R³ group have twogroups, one of which is the alkyl groups which may be substituted withhalogen atoms ranging from C₁ to C₁₀, preferably from C₁ to C₈,including a methyl group, an ethyl group, a n-propyl group, an isopropylgroup, a t-butyl group, a n-butyl group, an isobutyl group, a sec-butylgroup, a n-pentyl group, a 1-ethylpropyl group, a n-decyl group, achloromethyl group, a trifluoromethyl group, a trichloromethyl group, a1-bromoisopropyl group, a chlorodifluromethyl group, and1-chloromethyl-1-methylethyl group; and another one of which iscycloalkyl groups ranging from C₃ to C₈, preferably from C₃ to C₆,including a cyclopropyl group, a cyclobutyl group, a cyclopentyl group,and a cyclo-octyl group.

Examples of alkenyl groups ranging from C₂ to C₆ include a vinyl group,an allyl group, a butenyl group, and a hexenyl group; examples ofalkynyl groups ranging from C₂ to C₄ include an ethynyl group, apropargyl group, and a butynyl group; examples of the aralkyl groupsinclude a benzyl group and a 2-phenylethyl group; the lower alkyl groupssubstituted with an amino group include aminomethyl group and a1-aminoisobutyl group; example of aralkyl groups substituted with anamino group is a 1-amino-2-phenylethyl groups etc.; and examples of thelower alkyl groups substituted with an acylamino group include anacetylaminomethyl group and a 1-acetylaminoisobutyl group.

An example of an aralalkyl group substituted with an acylamino group isa 1-acetylamino-2-phenyl group; examples of lower alkyl groupssubstituted with an alkoxycarbonylamino group include at-butoxycarbonylaminomethyl group and a 1-(t-butoxycarbonyl amino)isobutyl group; and an example of aralkyl group substituted with analkoxycarbonylamino group is a 1-(benzyloxycarbonylamino)-2-phenylethylgroup.

Examples of the aryl groups which may be substituted with halogen atoms,lower alkyl groups which may be substituted with halogen atoms, a loweralkylthio group, an amino group, a nitro group or a cyano group includea phenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group, a4-fluorophenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a4-chlorophenyl group, a 2, 4-dichlorophenyl group, a 3, 4-dichlorophenylgroup, a 2, 6-dichlorophenyl group, a 4-methylphenyl group, a2-methylphenyl group, a 2, 4-dimethylphenyl group, a4-trifluoromethylphenyl group, a 2-methoxyphenyl group, a3-methoxyphenyl group, a 4-methoxyphenyl group, a 2-methylthiophenylgroup, a 4-aminophenyl group, a 4-acetylaminophenyl group, a2-cyanophenyl group, a 3-cyanophenyl group, a 4-cyanophenyl group, a4-nitrophenyl group, and a naphthyl group.

Examples of the heteroaryl groups include a 2-furyl group, a 2-thienylgroup, a pyridin-4-yl group, a pyridin-2-yl group, a thiazol-4-yl group,an oxazol-4-yl group, a pyrazol-3-yl group, an imidazol-4-yl group, anisothiazol-5-yl group, an isoxyazol-5-yl group, a pyrazinyl group, apyrimidin-2-yl group, a pyridazin-3-yl group, a (1, 2,3-thiaziazol)-4-yl group, a (1, 2, 5-thiaziazol)-3-yl group, afurazanyl, a benzothiazol-2-yl group, a benzothiazol-2-yl group, abenzoimidazol-2-yl group, a quinolin-2-yl group, an isoquinolin-2-ylgroup, and a quinoxalin-2-yl group.

Examples of the lower alkoxy groups include a methoxy group, an ethoxygroup, a n-propoxy group, an isopropoxy group, a butoxy group, at-butoxy group, and a 1-ethylpropoxy group; examples of thecycloalkyloxy groups ranging C₃ to C₆ include a cyclopropyloxy group, acyclopentyloxy group, and a cyclohexyloxy group; and an example of thearyloxy group is a phenoxy group. The substituting groups which aresubstitutable with the nitrogen atom and the carbon atom on the Het Cmay be two or more.

Preferable examples of Het C are groups such as a thiazol-2-yl groupwhich may be substituted, a thiazol-4-yl group which may be substituted,and a thiazol-4-yl group which may be substituted. The most preferableexamples are groups such as a thiazol-2-yl group, a thiazol-4-yl group,a 2-aminothiazol-4-yl group, a 2-acylaminothiazol-4-yl group, a2-alkoxycarbonylaminothiazol-4-yl group, a 2-alkoxythiazol-4-yl group, a2-alkylthiothiazol-4-yl group, 2-alkylsulfinylthiazol-4-yl group, a2-alkylsulfonylthiazol-4-yl group, a 2-arylthiazol-4-yl group, and a2-bromothiazol-4-yl group.

There are two solid structures, i.e., an “E” form and a “Z” form in theoxime portions in the oxime derivatives represented by the generalformulas (1) and (2). The solid structures of both the “E” and “Z” formsare included in the scope of the present invention. In general,synthesized products of oxime derivatives include both forms asmixtures, and it is possible to isolate by a separation and purificationprocesses.

Although the “Z” form of the oxime derivative is more effective as theplant disease control chemical than the “E” form, the “Z” form graduallychanges into the “E” form under ordinary conditions and the ratiobetween the “E” and “Z” forms is stabilized at a constant ratio. Theconstant ratio between the “E” and “Z” forms varies with the types ofoxime derivatives.

The oxime derivatives of the present invention, which are represented bythe general formulas (1) and (2) may be manufactured by, for example,the following methods. However, it is to be understood that the methodsof manufacturing the oxime derivatives of the present invention are notlimited to the methods described in the following manufacturingexamples.

Manufacturing Method A

(In the formula, the definitions of HetA, HetB, Het C, X, n, and R¹ arethe same as those defined hereinbefore.)

An oxime compound expressed by general chemical formulas (1) or (2) ismanufactured by the following steps of, obtaining a hydroxyiminocompound (b) by reacting an azole-methanone compound (a) withhydroxylamine; and reacting the obtained hydroxyimino compound withhalogenized compounds (c) or (d) in the presence of salts (such assodium hydride, sodium hydroxide, pottasium hydroxide, sodium carbonate,pottasium carbonate, cesium carbonate, triethylamine, pyridine,N,N-dimethylaminopyridine). As a process for synthesizing theazole-methanone compound, a process described in, for example,“Synthesis”, p. 976 (1982), is applicable.

The practical chemical structures of the compounds expressed by thegeneral formulas (1) and (2), and which are manufactured by the abovemanufacturing steps are shown in Tables 1 to 66.

TABLE 1

Het B:

(a)

(b) (c) No Het A R¹ Xn  1

H H  2

H H  3

H H  4

H H  5

H H  6

H H  7

H H  8

H H  9

H H 10

H H 11

H H 12

H H 13

H H 14

H H 15

H H 16

H H 17

H H 18

H H 19

H H 20

H H 21

H H 22

H H 23

H H 24

H H 25

H H 26

H H

TABLE 2

Het B:

(a)

(b) (c) No Het A R¹ Xn Y  1

H H CH₃  2

H H CH₃  3

H H CH₃  4

CH₃ H CH₃  5

C₂H₅ H CH₃  6

C₃H₇ H CH₃  7

H H C₂H₅  8

H 3-CF₃ C₃H₇  9

H H CH(CH₃)₂ 10

H H H

TABLE 3

Het B:

(a)

(b) No Het A R¹ Xn Y  1

H H CF₃  2

H 4-Cl CF₃  3

H 3-Cl CF₃  4

H 4-F CF₃  5

H 3-F CF₃  6

H H Cl  7

H 4-Cl Cl  8

H 3-Cl Cl  9

H 4-F Cl 10

H 3-F Cl

TABLE 4

Het B:

(a)

(b) (c) No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  62,5-(Cl)₂  7 2,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F12 3-F 13 4-F 14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 183,4-(F)₂ 19 3,5-(F)₂ 20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 242,3-(CH₃)₂ 25 2,4-(CH₃)₂ 26 2,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 293-Cl, 5-CH₃ 30 3-F, 5-CH₃ 31 3-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 352-CN 36 3-CN 37 4-CN 38 2-SMe 39 3-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 434-SO₂Me 44 2-Br 45 3-Br 46 4-Br 47 2-OH 48 3-OH 49 4-OH 50 2-OMe 513-OMe 52 4-OMe

TABLE 5

Het B:

(a)

(b) (c) No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  64-OCF₂H  7 2-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl13 3-CF₂Cl 14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 204-NH₂ 21 4-Ph 22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂27 2,6-(CF₃)₂ 28 3,4-(CF₃)₂ 29 2,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 322-Cl, 4-Me 33 2-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 6

Het B:

(a)

(b) (c) No Het C R¹ Xn  1

H H  2

H H  3

H H  4

H H  5

H H  6

H H  7

H H  8

H H  9

H H 10

H H 11

H H 12

H H 13

H H 14

H H 15

H H 16

H H 17

H H 18

H H 19

H H 20

H H 21

H H 22

H H 23

H H 24

H H 25

H H 26

H H

TABLE 7

Het B:

(a)

(b) (c) No Het C R¹ Xn  1

H H  2

H H  3

H H  4

H H  5

H H  6

H H  7

H H  8

H H  9

H H 10

H H 11

H H 12

CH₃ H 13

CH₃ H 14

CH₃ H 15

H H 16

H H 17

H H 18

H H 19

H H 20

H H 21

H H

TABLE 8

Het B:

(a)

(b) (c) No Het C R¹ Xn  1

H H  2

H H  3

H H  4

H H  5

H H  6

H H  7

H H  8

H H  9

H H 10

H H 11

H H 12

H H 13

H H 14

H H 15

H H 16

H H 17

H H 18

H H 19

H H 20

H H 21

H H 22

H H 23

H H 24

H H 25

H H

TABLE 9

Het B:

(a)

(b) (c) No Het C R¹ Xn  1

H H  2

H H  3

H H  4

H H  5

H H  6

H H  7

H H  8

H H  9

H H 10

H H 11

H H 12

H H 13

H H 14

H H 15

H H 16

H H 17

H H 18

H H 19

H H 20

H H 21

H H 22

H H 23

H H 24

H H 25

H H 26

H H

TABLE 10

Het B:

(a)

(b) (c) No Het C R¹ Xn  1

H H  2

H H  3

H H  4

H H  5

H H  6

H H  7

H H  8

H H  9

H H 10

H H 11

H H 12

H H 13

H H 14

H H 15

H H 16

H H 17

H H 18

H H 19

H H 20

H H 21

H H

TABLE 11

Het B:

(a)

(b) (c) No Het C R¹ Xn  1

H H  2

H H  3

H H  4

H H  5

H H  6

H H  7

H H  8

H H  9

H H 10

H H 11

H H 12

H H 13

H H 14

H H

TABLE 12

Het B:

(a)

(b) (c) No Het C R¹ Xn Y  1

C₂H₅ 3-Cl CH₃  2

C₃H₇ 4-Cl CH₃  3

C₄H₉ 4-F CH₃  4

C₂H₅ H CH₃  5

C₃H₇ H CH₃  6

C₄H₉ H CH₃  7

H H C₂H₅  8

H H C₂H₅  9

H H C₂H₅ 10

H 3-Cl C₃H₇ 11

H 4-Cl C₄H₉ 12

H 4-F C₄H₉ 13

H H CH(CH₃)₂ 14

H H CH(CH₃)₂ 15

H H CH(CH₃)₂

TABLE 13

Het B:

(a) (b) (c) No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  62,5-(Cl)₂  7 2,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F12 3-F 13 4-F 14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 183,4-(F)₂ 19 3,5-(F)₂ 20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 242,3-(CH₃)₂ 25 2,4-(CH₃)₂ 26 2,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 293-Cl, 5-CH₃ 30 3-F, 5-CH₃ 31 3-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 352-CN 36 3-CN 37 4-CN 38 2-SMe 39 3-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 434-SO₂Me 44 2-Br 45 3-Br 46 4-Br 47 2-OH 48 3-OH 49 4-OH 50 2-OMe 513-OMe 52 4-OMe

TABLE 14

Het B:

(a) (b) (c) No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  64-OCF₂H  7 2-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl13 3-CF₂Cl 14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 204-NH₂ 21 4-Ph 22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂27 2,6-(CF₃)₂ 28 3,4-(CF₃)₂ 29 2,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 322-Cl, 4-Me 33 2-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 15

Het B:

(a) (b) (c) No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  62,5-(Cl)₂  7 2,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F12 3-F 13 4-F 14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 183,4-(F)₂ 19 3,5-(F)₂ 20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 242,3-(CH₃)₂ 25 2,4-(CH₃)₂ 26 2,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 293-Cl, 5-CH₃ 30 3-F, 5-CH₃ 31 3-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 352-CN 36 3-CN 37 4-CN 38 2-SMe 39 3-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 434-SO₂Me 44 2-Br 45 3-Br 46 4-Br 47 2-OH 48 3-OH 49 4-OH 50 2-OMe 513-OMe 52 4-OMe

TABLE 16

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me,4-Cl 31 2-Me,3-Cl 32 2-Cl,4-Me 332-Et,6-Me 34 2-Cl,5-CF₃ 35 2-Cl,6-F 36 2,4,6-(Me)₃

TABLE 17

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl,5-CH₃ 30 3-F,5-CH₃ 313-F,5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 18

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me,4-Cl 31 2-Me,3-Cl 32 2-Cl,4-Me 332-Et,6-Me 34 2-Cl,5-CF₃ 35 2-Cl,6-F 36 2,4,6-(Me)₃

TABLE 19

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl,5-CH₃ 30 3-F,5-CH₃ 313-F,5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 20

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me,4-Cl 31 2-Me,3-Cl 32 2-Cl,4-Me 332-Et,6-Me 34 2-Cl,5-CF₃ 35 2-Cl,6-F 36 2,4,6-(Me)₃

TABLE 21

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl,5-CH₃ 30 3-F,5-CH₃ 313-F,5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 22

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me,4-Cl 31 2-Me,3-Cl 32 2-Cl,4-Me 332-Et,6-Me 34 2-Cl,5-CF₃ 35 2-Cl,6-F 36 2,4,6-(Me)₃

TABLE 23

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl,5-CH₃ 30 3-F,5-CH₃ 313-F,5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 24

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me,4-Cl 31 2-Me,3-Cl 32 2-Cl,4-Me 332-Et,6-Me 34 2-Cl,5-CF₃ 35 2-Cl,6-F 36 2,4,6-(Me)₃

TABLE 25

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 26 3,5-(CH₃)₂ 29 3-Cl,5-CH₃ 30 3-F,5-CH₃ 313-F,5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 26

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me,4-Cl 31 2-Me,3-Cl 32 2-Cl,4-Me 332-Et,6-Me 34 2-Cl,5-CF₃ 35 2-Cl,6-F 36 2,4,6-(Me)₃

TABLE 27

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl,5-CH₃ 30 3-F,5-CH₃ 313-F,5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 28

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me,4-Cl 31 2-Me,3-Cl 32 2-Cl,4-Me 332-Et,6-Me 34 2-Cl,5-CF₃ 35 2-Cl,6-F 36 2,4,6-(Me)₃

TABLE 29

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,4-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl,5-CH₃ 30 3-F,5-CH₃ 313-F,5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 30

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me,4-Cl 31 2-Me,3-Cl 32 2-Cl,4-Me 332-Et,6-Me 34 2-Cl,5-CF₃ 35 2-Cl,6-F 36 2,4,6-(Me)₃

TABLE 31

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl,5-CH₃ 30 3-F,5-CH₃ 313-F,5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 32

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 33

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl, 5-CH₃ 30 3-F, 5-CH₃ 313-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 34

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 35

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl, 5-CH₃ 30 3-F, 5-CH₃ 313-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 36

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 37

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl, 5-CH₃ 30 3-F, 5-CH₃ 313-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 38

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 39

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl, 5-CH₃ 30 3-F, 5-CH₃ 313-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 40

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 41

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl, 5-CH₃ 30 3-F, 5-CH₃ 313-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 42

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 43

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl, 5-CH₃ 30 3-F, 5-CH₃ 313-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 44

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 45

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl, 5-CH₃ 30 3-F, 5-CH₃ 313-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 46

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 47

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl, 5-CH₃ 30 3-F, 5-CH₃ 313-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 48

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 49

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl, 5-CH₃ 30 3-F, 5-CH₃ 313-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 50

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 51

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl, 5-CH₃ 30 3-F, 5-CH₃ 313-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 52

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 53

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl, 5-CH₃ 30 3-F, 5-CH₃ 313-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 54

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 55

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl, 5-CH₃ 30 3-F, 5-CH₃ 313-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 56

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 57

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl, 5-CH₃ 30 3-F, 5-CH₃ 313-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 58

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 59

No Xn  1 2-Cl  2 3-Cl  3 4-Cl  4 2,3-(Cl)₂  5 2,4-(Cl)₂  6 2,5-(Cl)₂  72,6-(Cl)₂  8 3,4-(Cl)₂  9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F14 2,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂20 2,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl, 5-CH₃ 30 3-F, 5-CH₃ 313-F, 5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 60

No Xn  1 2-OPh  2 3-OPh  3 4-OPh  4 2-OCF₂H  5 3-OCF₂H  6 4-OCF₂H  72-CO₂H  8 3-CO₂H  9 4-CO₂H 10 2-CO₂Me 11 3-CO₂Me 12 2-CF₂Cl 13 3-CF₂Cl14 4-CF₂Cl 15 2-NO₂ 16 3-NO₂ 17 4-NO₂ 18 2-NH₂ 19 3-NH₂ 20 4-NH₂ 21 4-Ph22 2-OCF₃ 23 3-OCF₃ 24 4-OCF₃ 25 2,4-(CF₃)₂ 26 2,5-(CF₃)₂ 27 2,6-(CF₃)₂28 3,4-(CF₃)₂ 29 3,5-(CF₃)₂ 30 2-Me, 4-Cl 31 2-Me, 3-Cl 32 2-Cl, 4-Me 332-Et, 6-Me 34 2-Cl, 5-CF₃ 35 2-Cl, 6-F 36 2,4,6-(Me)₃

TABLE 61

No Het C R¹ Xn  1

H H  2

H H  3

H H  4

H H  5

H H  6

H H  7

H H  8

H H  9

H H 10

H H 11

H H 12

H H 13

H H 14

H H 15

H H 16

H H 17

H H 18

H H 19

H H 20

H H 21

H H 22

H H 23

H H 24

H H 25

H H 26

H H

TABLE 62

No Het C R¹ Xn 1

H H 2

H H 3

H H 4

H H 5

H H 6

H H 7

H H 8

H H 9

H H 10

H H 11

H H 12

H H 13

H H 14

H H 15

H H 16

H H 17

H H 18

H H 19

H H 20

H H 21

H H 22

H H 23

H H 24

H H 25

H H 26

H H

TABLE 63

No Het C R¹ Xn 1

H H 2

H H 3

H H 4

H H 5

H H 6

H H 7

H H 8

H H 9

H H 10

H H 11

H H 12

H H 13

H H 14

H H 15

H H 16

H H 17

H H 18

H H 19

H H 20

H H 21

H H 22

H H 23

H H 24

H H 25

H H 26

H H

TABLE 64

No Het C R¹ Xn 1

H H 2

H H 3

H H 4

H H 5

H H 6

H H 7

H H 8

H H 9

H H 10

H H 11

H H 12

H H 13

H H 14

H H 15

H H 16

H H 17

H H 18

H H 19

H H 20

H H 21

H H 22

H H 23

H H 24

H H 25

H H 26

H H

TABLE 65

No Het C R¹ Xn 1

H H 2

H H 3

H H 4

H H 5

H H 6

H H 7

H H 8

H H 9

H H 10

H H 11

H H 12

H H 13

H H 14

H H 15

H H

TABLE 66

No Het C Xn Y 1

H CF₃ 2

4-Cl CF₃ 3

3-Cl CF₃ 4

4-F CF₃ 5

3-F CF₃ 6

H Cl 7

4-Cl Cl 8

3-Cl Cl 9

4-F Cl 10

3-F Cl

wherein, Het A, Het B, Het C, X, Y, n, and R¹ correspond to thosedefined in the general formulas (1) and (2), and Me represents a methylgroup, Et represents an ethyl group, Pr represents a propyl group, Burepresents a butyl group, and Ph represents a phenyl group.

Agricultural chemicals, particularly plant disease control chemicals,which contain the oxime derivatives according to the present inventionas active ingredients, are effective for various plant diseasesinvolving bacteria and mold fungi, and are particularly effective forplant diseases caused by mold fungi. The plant diseases caused by moldfungi include a wide range of types of plant diseases caused byOomycetes and plant diseases caused by Pyricularia oryzae.

The agricultural chemicals of the present invention are particularlyeffective for plant diseases such as downy-mildew and late-blight orPhytophthora rot of various plants, which include a wide variety ofplant diseases caused by Oomycetes such as Plasmopara viticola,Pseudoperonospora cubensis, Phytophthora melonis, Phytophthora capsici,Phythophthora infestans, Peronospora brassicae, Peronospora destructor,Peronospora spinaciae, and Peronospora manshurica;

and, Peronospora viciae, Phytophthora nicotianae var. nicotianae,Phytophtora infestans, Pseudoperonospora humuli, Phytophthora cinnamomi,Phytophthora capsici, Phytophthora fragariae, diseases for various farmproducts by Pythium bacteria, Pythium aphanidermatum, and Pyriculariaoryzae.

The agricultural chemicals of the present invention may be used alone,or, in general, may be used in combinations with known auxiliarysubstances such as solid and liquid carriers, dispersing agents,diluents, emulsifiers, spreaders, thickners. The agricultural chemicalsof the present invention may be used in the forms of wettable powder,solutions, oil solutions, powder, granules, and sol-type forms byformulation.

Examples of the solid and liquid carriers include, for example, talc,clay, bentonite, kaolin, diatomite, montmorillonite, micas, vermiculite,gypsum, calcium carbonate, white carbon, wood powder, starch, alumina,silicate salt, glycol polymer, waxes, water, alcohols (such as methylalcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butylalcohol, ethylene glycol, benzyl alcohol), petroleum fractions (such aspetroleum ether, kerosene, solvent naphtha), aliphatic and alicyclichydrocarbons (such as n-hexane, cyclohexane); and

aromatic hydrocarbons (such as benzene, toluene, xylene, ethylbenze,chlorobenzene, cumene, and methylnaphthalene), halogenized hydrocarbons(such as chloroform, dichloromethane), ethers (such as isopropyl ether,ethylene oxide, and tetrahydrofuran), ketones (such as acetone,methylethyl ketone, cyclohexane, and mthylisobutyl ketone), esters (suchas ethyl acetate, butyl acetate, ethyleneglycol acetate, and amylacetate), acid amides (such as dimethylforamide, anddimethylacetoanilide), nitriles (such as acetonitrile, prop ionitrile,acrylonitrile), sulfoxides (such as dimethylsulfoxide), alcohol ethers(such as ethyleneglycol monomethylether, and ethyleneglycolmonoethylether).

Examples of the auxiliary substances include, for example,non-ionic-type surface active agents (such as polyoxyethylenealkylether, polyoxyethylene alkylester, polyoxyethylenealkylphenylether, polyoxyethylene sorbitanalkylester, andsolbitanalkylester), anionic-type surface active agents (such asalkylbenzenesulfonate, alkylsulfosuccinate, polyoxyethylenealkylsulfate, and arylsulfonate), cationic-type surface active agentssuch as (alkylamines, polyoxyethylene alkylamines, and quarternaryammonium salts), amphoteric surfactants (such as alkylaminoethylglycineand alkyldimethylbetaine), polyvinyl alcohol, hydroxypropyl cellulose,carboxymethyl cellulose, gum arabic, tragacanth gum, xanthan gum,polyvinyl acetate, gelatin, casein, and sodium alginate.

Furthermore, the present agents may be used in combinations with knownagricultural chemicals such as agricultural and horticultural fungicide,herbicides, growth regulators of plants, insecticides, acaricides, andwith fertilizers. Although the contents of the present chemicals varydepending upon the forms of the chemicals, application methods, andother conditions, the effective content ranges from 0.5 to 95% byweight, and preferably, from 2 to 70% by weight.

Various methods may be applied, including application to foliage(foliage spraying), application to planting soil (soil treatment),application to the water surface of a field (water surface treatment),and application to seeds (seed treatment).

The amount of the present agricultural chemicals varies with the type ofplants to which it is applied and the disease in question. When thechemicals are applied to foliage, it is preferable to apply then using aliquid solution at a rate of 50 to 300 liters per 10 are at aconcentration of 1 to 10,000 ppm, preferably, 10 to 1,000 ppm as aneffective chemical concentration. For application to a water surface orsoil, it is preferable to apply 0.1 to 100 g per 10 are. When treatingseeds, it is preferable to apply 0.001 to 50 g of the presentagricultural chemicals per 1 kg of seed.

Hereinafter, the present invention will be described in more detailreferring to following examples in terms of manufacturing methods,formulation examples and test examples. It is to be understood that thepresent invention is not limited to the following examples.

MANUFACTURING EXAMPLE 1

Hydroxylamine hydrochloride (0.20 g, 2.82 mmol) and triethylamine (0.4ml, 2.8 mmol) were added to an ethanol solution (20 ml) of (5-methyl-1,2, 3-thiaziasol-4-yl) phenylmethanone (0.29g, 1.41 mmol) and heated for48 hours with refluxing. After concentrating the thus reacted solution,ethyl acetate was added to the residue, washed with water, and theresidue was dried with magnesium sulfate. The solvent was removed bydistillation and the residue was purified by column chromatography andyielded (Z)-(5-methyl-1, 2, 3-thiadiazol-4-yl)phenylmethanone oxime(0.16 g) and (E)-(5-methyl-1, 2, 3-thiadiazol-4-yl) phenyl methanoneoxime (0.04 g).

(Z)-(5-methyl-1, 2, 3-thiadiazol-4-yl)phenylmethanone oxime: ¹H-NMR(CDCl₃): δ 2.54 (s. 3H), 7.30˜7.50 (m. 5H), 8.30˜8.45 (brd. 1H). MS(m/e): 219 (M⁺);

(E)-(5-mthyl-1, 2, 3-thiadiazol-4-yl)phenylmethanone oxime: ¹H-NMR(CDCl₃): δ 2.54 (s. 3H), 7.35˜7.60 (m. 5H), 8.00˜8.20 (brd. 1H). MS(m/e): 219 (M⁺).

MANUFACTURING EXAMPLE 2

(Z)-(5-methyl-1, 2, 3-thiadiazol-4-yl)phenylmethanone oxime (9.31 g,0.04 mol) was dissolved in acetonitrile (677 ml), hydrochloride of2-picolylchloride (10.40 g, 0.07 mol) was added and heated for 5 hourswith refluxing. After concentrating the thus reacted solution, theresidue was extracted by ethyl acetate, and the extracted substance wasdried after washing by water. The solvent was removed by distillation,the residue was purified by column chromatography, and yielded(Z)-(5-methyl-1, 2, 3-thiadiazol-4-yl) phenylmethanoneO-(2-pyrydyl)-methyl oxime (9.67 g) (Compound No. 1-(a)-1(Z)).

¹H-NMR (CDCl₃): δ 2.53 (s. 3H), 5.40 (s. 2H), 7.19 (dd., J=4.9 Hz, J=7.6Hz, 1H), 7.30˜7.42 (m. 3H), 7.35 (d. J=7.8 Hz, 1H), 7.44˜7.50 (m. 2H),7.67 (J=7.8 Hz, J=7.6 Hz, 1H), 8.56 (d. J=4.9 Hz, 1H). MS (m/e): 310(M⁺).

MANUFACTURING EXAMPLE 3

(E)-(5-mthyl-1, 2, 3-thiadiazol-4-yl) phenylmethanone oxime (0.30 g, 1.4mmol) was dissolved in acetone (20 ml), potassium carbonate (0.32 g, 2.0mmol) and hydrochloride of 2-picolylchloride (0.34 g, 2.0 mmol) wereadded and heated for 3 days with refluxing. After concentrating the thusreacted solution, the residue was extracted with ethylacetate, and afterwashing with water, the residue was dried with magnesium sulfate. Thesolvent was removed by distillation, the residue was refined in a columnchromatography, and yielded (E)-(5-mthyl-1, 2,3-thiadiazol-4-yl)phenyl-methanone O-(2-pyridyl) methyloxime.

¹H-NMR (CDCl₃): δ 2.59 (s. 3H), 5.40 (s. 2H), 7.21 (dd., J=4.83 Hz,J=8.70 Hz, 1H), 7.31˜7.72 (m. 7H), 8.58 (J=4.88 Hz, 1H). MS (m/e): 310(M⁺).

MANUFACTURING EXAMPLE 4

Hydroxylamine hydrochloride (4.48 g, 63.1 mmol) and triethylamine (8.8ml, 63.1 mmol) were added to an ethanol solution (85 ml) of (3-methyl-1,2, 5-thiadiazol-4-yl) phenylmethane (3.22 g, 15.7 mmol) and heated for 8hours with refluxing. After the reacted solution was concentrated, ethylacetate/water was added to the residue for extraction. The residue wasdried with magnesiun sulfate, after the solvent was removed bydistillation. The residue was refined by column chromatography andyielded (Z)-(3-methyl-1, 2, 5-y thiadiazol-4-yl) phenylmethanone oxime(2.18 g).

¹H-NMR (CDCl₃): δ 2.53 (s. 3H), 7.27˜7.56 (m. 5H), 8.52˜8.78 (brd. 1H).MS (m/e): 219 (M⁺).

MANUFACTURING EXAMPLE 5

60% sodium hydride (2.41 g, 60.0 mmol) was added to DMF (150 ml)(N,N-Dimethyl-foramide) and cooled by ice, and (Z)-(3-methyl-1, 2,5-thiadiazol-4-yl) pheylmethane-oxime was then added and stirred for 40minutes. A DMF (110 ml) solution of4-chloromethyl-2-iso-propionylaminothiazole (7.76 g, 35.6 mmol) wasadded dropwise to the thus reacted solution. After the reacted solutionwas gradually restored to the room temperature, it was stirred for 20hours. The solvent in the reacted solution was removed under a reducedpressure and ethyl-acetate/water was added to the residue forextraction. The extracted solution was dried with magnesium sulfateafter washing by water. The solvent was removed by distillation, and theresidue was refined by column chromatography, and yielded(Z)-(3-methyl-1, 2, 5-thiadiazol-4-yl) pheylmethaneO-(2-iso-propionylaminothiazol-4-yl) methyloxime.

¹H-NMR (CDCl₃): δ 1.22 (d. J=6.91 Hz, 6H), 2.41 (s. 3H), 2.47˜2.76 (m.1H), 5.21 (s. 2H), 6.89 (s. 1H) 7.28˜7.60 (m. 5H), 9.50˜9.90 (brd. 1H).MS (m/e): 401 (M⁺).

MANUFACTURING EXAMPLE 6

A pyridine (55 ml) solution of hydroxylamine hydrochloride (5.19 g, 73.0mmol) was added to (3-methyl-1, 2, 5-oxadiazol-4-yl) phenylmethanone(3.43 g, 18.0 mmol) and heated to 70° C. for 21 hours with stirring.After the reacted solution was condensed, the residue was dissolved inethyl acetate. After washing with diluted hydrochloride and subsequentwashing with water, the residue was dried with magnesium carbonate.After removing the solvent and purifying the residue by columnchromatography, (Z)-(3-methyl-1, 2, 5-oxadiazol-4-yl) phenylmethanoneoxime (2.13 g) and (E)-(3-methyl-1, 2, 5-oxadiazol-4-yl)phenylmethanoneoxime (0.79 g) were obtained.

(Z)-(3-methyl-1, 2, 5-oxadiazol-4-yl) phenylmethanone oxime: ¹H-NMR(CDCl₃): δ 2.38 (s. 3H), 7.30˜7.62 (m. 2H), 7.89˜8.00 (brd. 1H). MS(m/e): 219 (M⁺). (E)-(3-methyl-1, 2, 5-oxadiazol-4-yl)phenylmethanoneoxime: ¹H-NMR (CDCl₃): δ 2.55 (s. 3H), 7.48˜7.62 (m. 2H), 7.89˜8.00(brd. 1H). MS (m/e): 219 (M⁺).

MANUFACTURING EXAMPLE 7

60% sodium hydride (0.43 g, 10.6 mmol) was added to DMF (16 ml) andcooled by ice, and a DMF (20ml) solution of (Z)-(3-methyl-1, 2,5-oxadiazol-4-yl) phenylmethanone oxime (0.94 g, 4.36 mmol) was added tothat solution with stirring. A DMF (15 ml) solution of4-chloromethyl-2-triphenylmethylaminothiazole (2.71 g, 6.94 mmol) wasadded to the above reacted solution. After the reacted solution wasrestored to the room temperature, the reacted solution was stirred forfour days. The solvent of the solution was then removed under reducedpressure and added to ethyl acetate/water to the residue for extraction.The solvent was removed by distillation, the residue was refined bycolumn chromatography, and yielded (Z)-(3-methyl-1, 2, 5-oxadiazol-4-yl)phenylmethanone O-(2-triphenylmethylaminethiazol-4-yl) methyloxime (0.59g) (Compound No. 9-(c)-6 (Z)).

¹H-NMR (CDCl₃): δ 2.23 (s. 3H), 5.11 (s. 2H), 6.27 (s. 1H), 6.80˜6.97(brd. 1H), 7.13˜7.60 (m. 20H). MS (m/e): 557 (M⁺).

MANUFACTURING EXAMPLE 8

1M hydrochloride (0.6 ml) was added to an acetone (15 ml) solution of(Z)-(3-methyl-1, 2, 5-oxadiazol-4-yl) phenylmethanoneO-(2-triphenylmethylaminethiazol-4-yl) methyloxime, and heated for 8hours with refluxing. The solvent of the reacted solution was removedunder reduced pressure, and a solution of ethyl acetate/saturatedsolution of sodium hydrogencarbonate was added and extracted after thesolution was adjusted to pH=7. The extracted solution was washed withwater and the residue was dried with magnesium sulfate. The solvent wasremoved by distillation and the residue was refined by columnchromatography and yielded (Z)-(3-methyl-1, 2, 5-oxadiazol-4-yl)phenylmethanone O-(2-aminethiazol-4-yl) methyloxime (0.05 g) (CompoundNo. 8-(c)-1 (Z)).

¹H-NMR (CDCl₃): δ 2.31 (s. 3H), 4.85˜5.10 (brd. 1H), 5.14 (s. 2H), 6.46(s. 1H), 7.32˜7.66 (m. 5H). MS (m/e): 315 (M⁺).

MANUFACTURING EXAMPLE 9

Trifluoroacetic acid anhydride (7 ml) was added to (Z)-(3-methyl-1, 2,5-oxadiazol-4-yl) phenylmethanone O-(2-aminethiazol-4-yl) methyloxime(0.053 g, 0.168 mmol) and heated for 2 hours with stirring. The reactedsolution was concentrated, the residue was refined by columnchromatography and yielded (Z)-(3-methyl-1, 2, 5-oxadiazol-4-yl)phenylmethanone O-(2-trifluoroacetylaminethiazol-4-yl) methyloxime(0.063 g) (Compound No. 8-(c)-14 (Z)).

¹H-NMR (CDCl₃): δ 2.26 (s. 3H), 5.26 (s. 2H), 7.07 (s. 1H), 7.28˜7.56(m. 5H), 768˜8.10 (brd. 1H). MS (m/e): 411 (M⁺).

Physical and chemical data such as ¹H-NMR spectra and mass spectra ofoxime derivatives obtained by the same manufacturing methods as thoseshown in the above manufacturing examples are summarized in Tables 67 to81.

TABLE 67 Compound Table-(a), MS (b), (c)- (m/e, No.   E/Z ¹H-NMR (CDCl₃)δ M⁺) 1-(a)-1  Z 2.53 (s, 3H), 5.40 (s, 2H), 7.19 (dd, J = 4.9Hz, 310 J= 7.6Hz, 1H), 7.30-7.42 (m, 3H), 7.35 (d, J = 7.8Hz, 1H)1 7.44-7.50 (m,2H), 7.67 (dd, J = 7.8, 7.6Hz, 1H), 8.56 (d, J = 4.9Hz, 1 H). 1-(a)-1  E2.59 (s, 3H), 5.40 (s, 2H), 7.21 (dd, J = 4.83, 310 8.70Hz, 1H),7.31-7.72 (m, 7H), 8.58 (d, J = 4.88Hz, 1H). 1-(b)-1  Z 2.47 (s, 3H),5.36 (s, 2H), 7.19 (dd, J = 4.85Hz, 311 J = 7.40Hz, 1H), 7.30-7.50 (m,6H), 7.67 (t, J = (M⁺ + 7.64Hz, 1H), 8.56 (d, J = 4.80Hz, 1H). 1)1-(b)-1  E 2.60 (s, 3H), 5.40 (s, 2H), 7.15-7.55 (m, 7H), 311 7.70 (t, J= 7.60Hz, 1H), 8.59 (d, J = 4.80Hz, 1H). (M⁺ + 1) 1-(c)-1  Z 2.32 (s,3H), 5.41 (s, 2H), 7.15-7.60 (m, 7H), 294 7.69 (t, J = 774Hz, 1H), 8.56(d, J = = 4.81Hz, 1H). 1-(a)-2  Z 2.42 (s, 3H), 5.26 (s, 2H), 7.25-7.50(m, 6H), 310 7.70 (d, J = 10.2Hz, 1H), 8.56 (d, J = 4.84Hz, 1H), 8.62(s, 1H). 1-(a)-2  E 2.56 (s, 3H), 5.27 (s, 2H), 7.28-7.52 (m, 6H), 3107.70-7.78 (m, 1H), 8.57 (d, J = 4.82Hz, 1H), 8.65(s, 1H). 1-(a)-3  Z2.48 (s, 3H), 5.26 (s, 2H), 7.22 (d, J = 5.91Hz, 2H), 310 7.29-7.50 (m,5H), 8.58 (d, J = 6.03Hz, 2H). 1-(a)-3  E 2.55 (s, 3H), 5.27 (s, 2H),7.25 (d, J = 8.00Hz, 2H) 310 7.30-7.60 (m, 5H), 8.59 (d, J = 8.00Hz,2H). 1-(a)-4  Z 2.55 (s, 3H)1 5.36 (s, 2H), 7.30-7.54 (m, 6H), 311 8.71(d, J = 5.00Hz, 1H), 9.16 (s, 1H). 1-(a)-5  Z 2.52 (s, 3H), 5.41 (s,2H), 7.30-7.55 (m, 5H), 312 8.49-8.60 (m, 2H), 8.67 (s, 1H). (M⁺ + 1)1-(a)-8  Z 2.54 (s, 6H), 5.36 (s, 2H), 7.05 (d, J = 7.56Hz, 1H), 3247.12 (d, J = 7.58Hz, 1H), 7.30-7.62 (m, 6H). 1-(a)-9  Z 2.32 (s, 3H),2.51 (s, 3H), 5.35 (s, 2H), 7.14-7.55 324 (m, 7H), 8.39 (s, 1H).

TABLE 68 Compound Table-(a), MS (b), (c)- (m/e, No.   E/Z ¹H-NMR (CDCl₃)δ M⁺) 1-(b)-9  Z 2.32 (s, 3H), 2.47 (s, 3H), 5.33 (s, 2H) 324 7.18 (d, J= 7.94Hz1 1H), 7.27-7.56 (m, 6H), 8.39 (s, 1H). 1-(b)-9  E 2.34 (s, 3H),2.62 (s, 3H), 5.36 (s, 2H), 7.12-7.63 324 (m, 7H), 8.32-8.49 (m, 1H).1-(c)-9  Z 2.31 (s, 3H), 2.33 (s, 3H), 5.36 (s, 2H), 7.19 (d, 308 J =7.90Hz, 1H), 7.30-7.60 (m, 6H), 8.41 (s, 1H). 1-(c)-9  E 2.34 (s, 3H),2.43 (s, 3H), 5.36 (s, 2H), 7.20 (d, J = 308 7.90Hz, 1H), 7.39-7.69 (m,6H), 8.42 (s, 1H). 1-(a)-10  Z 2.49 (s, 3H), 2.54 (s, 3H), 5.23 (s, 2H),7.03 (d, J = 324 5.33Hz, 1H), 7.07 (s, 1H), 7.26-7.54 (m, 5H), 8.45 (d,J = 4.79 Hz, 1H). 1-(a)-12  Z 2.54 (s, 3H), 5.35 (s, 2H), 7.18-7.52 (m,7H), 344 7.64(t, J = 7.80Hz, 1H). 1-(a)-16  Z 2.55 (s, 3H), 5.31 (s,2H), 6.83 (dd, J = 2.48Hz, 329 J = 7.81Hz, 1H), 7.22 (dd, J = 1.92Hz, J= 7.46Hz, (M⁺ + 1H), 7.30-7.56 (m, 5H), 7.77 (dd, J = 7.62Hz, 1) 7.95Hz,1H). 2-(a)-1  Z 2.53 (s, 3H), 5.57 (s, 2H), 7.25-7.40 (m, 3H), 3607.41-7.60 (m, 4H), 7.64-7.77 (m, 1H), 7.80 (d, J = 8.30Hz, 1H), 8.07 (d,J = 8.26Hz, 1H), 8.16 (d, J = 8.50Hz, 1H). 2-(8)-3  Z 2.54 (s, 3H), 5.59(s, 2H), 7.30-7.60 (m, 5H), 361 7.65-7.92 (m, 2H), 7.98-8.37 (m, 2H),8.97 (s, 1H). 2-(a)-4  Z 1.59 (d, J = 6.76Hz, 3H), 2.55 (s, 3H), 3255.55 (q, J = 6.73Hz, 1H), 7.10-7.50 (m, 7H), (M⁺ + 7.65 (t, J = 7.75Hz,1H), 8.55 (d, J = 4.81Hz, 1H). 1) 2-(b)-4  Z 1.58 (d, J = 6.78Hz, 3H),2.51 (s, 3H), 324 5.52 (q, J = 6.72, 1H), 7.10-7.50 (m, 7H), 7.64 (t, J= 7.71Hz, 1H), 8.50-8.63 (m, 1H).

TABLE 69 Compound Table-(a), MS (b), (c)- (m/e, No.   E/Z ¹H-NMR (CDCl₃)δ M⁺) 2-(a)-7  Z 1.29 (t, J = 7.60Hz, 3H), 2.90 (q J = 7.60Hz, 2H), 3245.39 (s, 2H), 7.13-7.27 (m, 1H), 7.30-7.54 (m, 6H), 7.67 (t, J = 7.64Hz,1H), 8.57 (d, J = 4.84Hz, 1H). 2-(b)-7  Z 1.26 (t, J = 7.49Hz, 3H), 2.80(q, J = 7.49Hz, 2H), 324 5.36 (s, 2H), 7.10-7.80 (m, 8H), 8.50-8.63 (m,1H). 2-(b)-7  E 1.27 (t, J = 7.50Hz, 3H), 2.96 (q, J = 7.50Hz, 2H), 3245.41 (s, 2H), 7.10-7.80 (m, 8H), 8.50-8.63 (m, 1H). 2-(c)-7  Z 1.22(t, J= 7.55Hz, 3H), 2.70 (, J = 7.55Hz, 2H), 309 5.40 (s, 2H), 7.13-7.81 (m,8H), (M⁺ + 8.50-8.70 (m, 1H). 1) 2-(a)-10  ¹⁾ 4.14 (s, 2H), 6.45 (s,1H), 6.65 (t, J = 7.72Hz, 1H), 296 7.12-7.25 (m, 1H), 7.34 (d, J =7.85Hz, 1H), 7.45- 7.50 (m, 3H), 7.70-7.80 (m, 2H), 8.57 (d, J = 5.16Hz, 1H). 3-(b)-1  ¹⁾ 5.34 (s, 2H), 7.10-7.60 (m, 7H), 7.67 (m, 1H), 8.55364 (d, J = 5.41Hz, 1H). 3-(b)-6  Z 5.45 (s, 2H), 7.10-7.25 (m, 1H),7.31-7.61 (m, 6H), 331 7.69 (t, J = 7.74Hz, 1H), 8.58 (d, J = 3.98Hz,1H). 3-(b)-6  E 5.39 (s, 2H), 7.12-7.28 (m, 1H), 7.30-7.60 (m, 6H), 3317.62-7.76 (m, 1H). 3-(a)-7  ²⁾ 5.55 (s, 2H), 7.20-7.40 (m, 1H), 7.41 (d,J = 352 8.70Hz, 2H), 7.40-7.60 (m, 1H), 7.73 (d, J = 8.70Hz, 2H),7.64-7.82 (m, 1H), 8.61 (d, J = 4.61Hz, 1H). 4-(a)-1  E 2.67 (s, 3H),5.38 (s, 2H), 7.15-7.3 (m, 1H), 7.3- 344 7.55 (m, 5H), 7.6-7.8 (m, 1H),8.5-8.65 (m, 1H). 4-(a)-2  Z 2.53 (s, 3H), 5.40 (s, 2H), 7.20 (m, 1H),7.25- 344 7.45 (m, 4H), 7.51 (m, 1H), 7.69 (ddd, J = 1.8, 1.8, 7.7 Hz,1H), 8.56 (m, 1H). ¹Stereochemistry is unidentified.

TABLE 70 Compound Table-(a), MS (b), (c)- (m/e, No.   E/Z ¹H-NMR (CDCl₃)δ M⁺) 4-(a)-2  E 2.61 (s, 3H), 5.40 (s, 2H), 7.22 (m, 1H), 7.34 (d, 344J = 7.7 Hz, 1H), 7.4 (m, 3H), 7.55 (m, 1H), 7.71 (ddd, J = 1.8, 1.8, 7.7Hz, 1H), 8.59 (m, 1H). 4-(a)-3  Z 2.52 (s, 3H), 5.39 (s, 2H), 7.21 (dd,J = 4.7, 7.7 Hz, 344 1H), 7.26-7.36 (m, 3H), 7.42 (ddd, J = 2.2, 2.2,8.7 Hz, 2H), 7.67 (ddd, J = 1.8, 7.7, 7.7 Hz, 1H), 8.56 (d, J = 4.7 Hz,1H). 4-(a)-3  E 2.61 (s, 3H), 5.40 (s, 2H), 7.22 (dd, J = 4.8, 7.7 Hz,344 1H), 7.33 (d, J = 7.7 Hz, 1H), 7.43 (ddd, J = 2.0, 2.0, 8.8 Hz, 2H),7.52 (ddd, J = 2.0, 2.0, 8.8 Hz, 2H), 7.70 (ddd, J = 1.8, 7.7, 7.7 Hz,1H), 8.59 (m, 1H). 4-(b)-3  Z 2.47 (s, 3H), 5.36 (s, 2H), 7.15-7.5 (m,6H), 7.67 343 (m, 1H), 8.58 (m, 1H). (M⁺ − 1) 4-(a)-12  Z 2.53 (s, 3H),5.40 (s, 2H), 7.01-7.40 (m, 6H), 7.62- 328 7.72 (m, 1H), 8.55 8.59 (m,1H). 4-(a)-12  E 2.61 (s, 3H), 5.40 (s, 2H), 7.09 7.50 (m, 6H), 7.66-328 7.75 (m, 1H), 8.58-8.81 (m, 1H). 4-(a)-13  Z 2.53 (s, 3H), 5.38 (s,2H), 7.03 (dd, J = 8.7, 8.7 Hz, 328 2H), 7.20 (dd, J = 4.8, 7.8 Hz, 1H),7.31 (d, J = 7.8 Hz, 1H), 7.46 (dd, J = 5.4, 8.7 Hz, 2H), 7.87(ddd, J =1.7, 7.8, 7.8 Hz, 1H), 8.57 (d, J = 4.8 Hz, 1H). 4-(a)-13  E 2.60 (s,3H), 5.40 (s, 2H), 7.14 (dd, J = 8.8, 8.8 Hz, 328 2H), 7.21 (m, 1H),7.35(d, J = 7.8 Hz, 1H), 7.59 (dd, J = 5.4, 8.8 Hz, 2H), 7.70 (ddd, J =1.7, 7.8, 7.8 Hz, 1H), 8.59 (d, J = 4.8 Hz, 1H). 4-(b)-13  Z 2.48 (s,3H), 5.36 (s, 2H), 7.03 (t, J = 8.64Hz, 2H, 329 7.10-7.32 (m, 2H),7.36-7.60 (m, 2H), 7.67 (t, J = (M⁺ + 7.66Hz, 1H), 8.57 (d, J = 4.86Hz,1H). 1)

TABLE 71 Compound Table-(a), MS (b), (c)- (m/e, No.   E/Z ¹H-NMR (CDCl₃)δ M⁺) 4-(b)-13  E 2.61 (s, 3H), 5.40 (s, 2H), 7.00-7.75 (m, 7H), 8.50-329 8.60(m, 1H). (M⁺ + 1) 4-(b)-15  Z 2.56 (s, 3H), 5.38 (s, 2H), 6.77(m, 1H), 6.93 (ddd, 347 J = 2.5. 8.9, 8.9 Hz, 1H), 7.23 (m, 1H), 7.28(d, J = (M⁺ + 8.7 Hz, 1H), 7.6-7.8 (m, 2H), 8.59 (d, J = 4.9 Hz, 1) 1H).4-(a)-19  Z 2.54 (s, 3H), 5.40 (s, 2H), 6.78-6.90 (m, 1H), 6.92- 3467.08 (m, 2H), 7.16-7.34 (m, 2H), 7.62-7.75 (m, 1H), 8.52-8.62 (m, 1H).4-(a)-19  E 2.62 (s, 3H), 5.40 (s, 2H), 6.78-7.38 (m, 5H), 7.63- 3467.78 (m, 1H), 8.53-8.62 (m, 1H). 4-(a)-22  Z 2.33 (s, 3H), 2.52 (s, 3H),5.40 (s, 2H), 7.17-7.41 324 (m, 6H), 7.61-7.77 (m, 1H), 8.52-8.62 (m,1H). 4-(b)-23  Z 2.35 (s, 3H), 2.47 (s, 3H), 5.35 (s, 2H), 6.90-7.48 324(m, 6H), 7.66 (t, J = 7.67Hz, 1H), 8.56 (d, J = 4.73Hz, 1H). 4-(b)-23  E2.41 (s, 3H), 2.59 (s, 3H), 5.40 (s, 2H), 6.90-7.75 324 (m, 7H),8.50-8.75 (m, 1H). 4-(a)-33  Z 2.55 (s, 3H), 5.43 (s, 2H), 7.22 (dd, J =4.7, 7.0 Hz, 378 1H), 7.32 (d, J = 7.8 Hz, 1H), 7.47 (t, J = 7.8 Hz,1H), 7.58-7.78 (m, 3H), 7.81 (s, 1H), 8.58 (d, J = 4.7 Hz, 1H). 4-(b)-50 Z 2.60 (s, 3H), 3.47 (s, 3H), 5.37 (s, 2H), 6.82 (d, J = 340 8.3 Hz,1H), 6.95-7.5 (m), 7.55-7.75 (m), 8.57 (m, 1H). 4-(a)-52  Z 2.52 (s,3H), 3.81 (s, 3H), 5.37 (s, 2H), 6.86 (d, J = 340 8.9 Hz, 2H), 7.19 (dd,J = 4.7, 7.3 Hz, 1H), 7.32 (d, J = 7.8 Hz, 1H), 7.40 (d, J = 8.9 Hz,2H), 7.67 (ddd, J = 1.8, 7.3, 7.8 Hz, 1H), 8.55 (d, J = 4.7 Hz, 1H).

TABLE 72 Compound Table-(a), MS (b), (c)- (m/e, No.   E/Z ¹H-NMR (CDCl₃)δ M⁺) 4-(a)-52  E 2.57 (s, 3H), 3.85 (s, 3H), 5.41 (s, 2H), 6.96 (d, J =340 8.8 Hz, 2H), 7.21 (dd, J = 4.8, 7.3 Hz, 1H), 7.39 (d, J = 7.8 Hz,1H), 7.58 (d, J = 8.8 Hz, 2H), 7.69 (ddd, J = 1.7, 7.3, 7.8 Hz, 1H),8.59 (d, J = 4.8 Hz, 1H). 4-(b)-52  Z 2.41 (s, 3H), 3.82 (s, 3H), 5.34(s, 2H), 340 6.85 (d, J = 8.90Hz, 2H), 7.16-7.35 (m, 2H), 7.36 (d, J =8.90Hz, 2H), 7.67 (t, J = 7.50Hz, 1H), 8.50-8.60 (m, 1H). 4-(b)-52  E2.57 (s, 3H), 3.86 (s, 3H), 5.41 (s, 2H), 340 7.00 (d, J = 9.00Hz, 2H),7.16-7.35 (m, 2H), 7.52 (d, J = 9.00Hz, 2H), 7.60.-7.75 (m, 1H),8.50-8.65 (m, 1H). 4-(c)-52  Z 2.32 (s, 3H), 3.82 (s, 3H), 5.37 (s, 2H),324 6.88 (d, J = 8.96Hz, 2H), 7.17-7.41 (m, 2H), 7.47 (d, J = 8.96Hz,2H), 7.60-7.28 (m, 1H), 8.50-8.62 (m, 1H). 5-(a)-17  Z 2.55 (s, 3H),5.45 (s, 2H), 7.18-7.4 (m, 2H), 7.5- 355 7.9 (m, 3H), 8.02 (m), 8.20(m), 8.2-8.4 (m), 8.59 (m, 1H). 5-(b)-21  Z 2.51 (s, 3H), 5.39 (s, 2H),7.10-7.80 (m, 12H), 386 8.57 (d, J = 4.63Hz, 1H). 5-(b)-21  E 2.62 (s,3H), 5.44 (s, 2H), 7.10-7.80 (m, 12H), 386 8.57-8.68 (m, 1H). 5-(a)-24 Z 2.54 (s, 3H), 5.40 (s, 2H), 7.12-7.34 (m, 4H), 7.43- 394 7.57 (m,2H), 7.60-7.73 (m, 1H), 8.51-8.61 (m, 1H). 5-(a)-24  E 2.62 (s, 3H),5.40 (s, 2H), 7.16-7.38 (m, 4H), 7.56- 394 7.74 (m, 3H), 8.55-8.63 (m,1H). 5-(a)-29  Z 2.57 (s, 3H), 5.46 (s, 2H), 7.19-7.33 (m, 2H), 7.62-446 7.75 (m, 1H), 7.86-7.97 (m, 3H), 8.53-8.62 (m, 1H). 5-(a)-29  E 2.70(s, 3H), 5.41 (s, 2H), 7.19-7.33 (m, 2H), 7.61- 446 7.76 (m, 1H),7.91-8.03 (m, 3H), 8.55-8.62 (m, 1H).

TABLE 73 Compound Table-(a), (b), (c)- MS No.   E/Z ¹H-NMR (CDCl₃) δ(m/e, M⁺) 6-(b)-2  Z 2.36 (s, 3H), 5.20 (s, 2H), 7.04 (s, 1H), 2997.25-7.45 (m, 5H), 7.55 (s, 1H). 6-(b)-4  Z 2.35 (s, 3H), 5.28 (s, 2H),6.33 (d, J = 2.1Hz, 299 1H), 7.25-7.5 (m, 5H), 7.51 (d, J = 2.1Hz, 1H).6-(b)-6  Z 2.40 (s, 3H), 5.40 (s, 2H), 7.3-7.5 (m, 5H), 299 8.06 (s,1H). (M⁺ − 1) 6-(a)-18  Z 2.48 (s, 3H), 5.45 (s, 2H), 7.28-7.54 (m, 6H),316 8.76 (d, J = 2.01Hz, 1H). 6-(b)-18  Z 2.43 (s, 3H), 5.42 (s, 2H),7.26-7.53 (m, 6H), 316 8.78 (d, J = 2.02Hz, 1H). 6-(b)-18  E 2.66 (s,3H), 5.45 (s, 2H), 7.18-7.58 (m, 6H), 316 8.82 (d, J = 1 .99Hz, 1H).6-(c)-18  Z 2.28 (s, 3H), 5.46 (s, 2H), 7.26-7.60 (m, 6H), 300 8.80 (d,J = 1 .99Hz, 1H). 6-(a)-19  Z 2.50 (s, 3H), 5.54 (s, 2H), 7.30-7.60 (m,6H), 316 7.78 (d, J = 3.24Hz, 1H). 6-(b)-19  Z 2.44 (s, 3H), 5.51 (s,2H), 7.30-7.60 (m, 6H), 316 7.78 (d, J = 3.34Hz, 1H). 6-(b)-19  E 2.69(s, 3H), 5.54 (s, 2H), 7.30-7.60 (m, 6H), 316 7.81 (d, J = 3.35Hz, 1H).6-(a)-21  Z 2.41 (s, 3H), 5.79 (s, 2H), 7.33-7.62 (m, 5H), 317 8.64 (s,1H). 6-(a)-21  E 2.61 (s, 3H), 5.81 (s, 2H), 7.35-7.60 (m, 5H), 317 8.53(s, 1H).

TABLE 74 Compound Table-(a), MS (b), (c)- (m/e, No.   E/Z ¹H-NMR (CDCl₃)δ M⁺) 7-(a)-6  Z 2.55 (s, 3H), 5.63 (s, 2H), 7.33-7.60 (m, 7H), 366 7.90(d, d = 8.00Hz, 1H), 8.03 (d, J = 8.10Hz, 1H). 7-(a)-8  Z 2.39 (s, 3H),5.56 (s, 2H), 7.10-7.50 (m, 9H), 349 7.53-7.70 (brd, 1H). 7-(b)-8  Z2.42 (s, 3H), 5.52 (s, 2H), 7.20-7.60 (m, 9H), 349 7.60-7.90 (brd, 1H).7-(a)-10  Z 2.51 (s, 3H), 5.46 (s, 2H), 6.74 (t, J = 6.75Hz, 1H), 3497.13 (t, J = 6.96Hz, 1H), 7.30-7.60 (m, 7H). 8.05 (d, J = 6.75Hz, 1H).7-(b)-10  Z 2.47 (s, 3H), 5.44 (s, 2H), 6.75 (t, J = 6.57Hz, 1H), 3497.15(t, J = 6.64Hz, 1H), 7.30-7.70 (m, 7H), 8.05 (d, J = 6.80Hz, 1H).8-(a)-1  Z 2.50 (s, 3H), 4.90-5.15 (brd, 2H), 5.13 (s, 2H), 332 6.45 (s,1H), 7.29-7.55 (m, 5H). (M⁺ + 1) 8-(b)-1  Z 2.45 (s, 3H), 5.09 (s, 2H),5.20-5.38 (brd, 2H), 331 6.39 (s, 1H), 7.30-7.52 (m, 5H). 8-(b)-1  E2.68 (s, 3H), 5.10 (s, 2H), 5.39-5.50 (brd, 2H), 331 6.40 (s, 1H),7.30-7.52 (m, 5H). 9-(c)-1  Z 2.31 (s, 3H), 4.83-510 (brd, 1H), 5.14 (s,2H), 315 6.46 (s, 1H), 7.32-7.66 (m, 5H). 8-(b)-2  Z 2.35 (s, 3H), 5.20(s, 2H), 6.99 (s, 1H), 359 7.30-7.50 (m, 5H), 8.33 (m, 1H). 8-(b)-3  Z2.15 (s, 3H), 2.38 (s, 3H), 5.22 (s, 2H), 6.91 (s, 1H) 373 7.30-7.55 (m,5H). 8-(b)-3  E 2.15 (s, 3H), 2.64 (s, 3H), 5.24 (s, 2H), 6.92 (s, 1H)373 7.30-7.55 (m, 5H).

TABLE 75 Compound Table-(a), MS (b), (c)- (m/e, No.   E/Z ¹H-NMR (CDCl₃)δ M⁺) 8-(b)-4  Z 1.21 (t, J = 7.48Hz, 3H), 2.39 (s, 3H), 387 2.42 (q, J= 7.48Hz, 2H), 5.21 (s, 2H), 6.89 (s, 1H) 7.28-7.50 (m, 5H). 8-(b)-4  E1.25 (t, J = 7.57Hz, 3H), 2.42 (s, 3H), 387 2.46 (q, J = 7.57Hz, 2H),5.21 (s, 2H), 6.88 (s, 1H) 7.29-7.57 (m, 5H). 8-(a)-7  Z 1.25 (d, J =6.95Hz, 6H), 2.46 (s, 3H), 401 2.50-2.70 (m, 1H), 5.24 (s, 1H), 6.91 (s,1H), 7.28-7.50 (m, 5H), 9.20-9.45 (brd, 1H). 8-(b)-7  Z 1.22 (d, J =6.91Hz, 6H), 2.41 (s, 3H), 401 2.47-2.76(m, 1H), 5.21 (s, 2H), 6.89 (s,1H), 7.28-7.60 (m, 5H), 9.50-9.90 (brd, 1H). 8-(c)-7  Z 1.27 (d, J =6.95Hz, 6H), 2.28 (s, 3H), 385 2.50-2.75 (m, 1H), 5.25 (s, 2H), 6.91 (s,1H), 7.30-7.62 (m, 5H), 8.90-9.10 (brd, 1H). 8-(b)-8  Z 0.97 (d, J =6.39Hz, 6H), 2.08-2.36 (m, 3H), 415 2.41 (s, 3H), 5.22 (s, 2H), 6.87 (s,1H), 7.30-7.52 (m, 5H), 9.54-9.80 (brd, 1H). 8-(c)-8  Z 0.97 (d, J =6.45Hz, 6H), 2.20-2.30 (m, 3H), 399 2.25 (s, 3H), 5.25 (s, 2H), 6.91 (s,1H), 7.30-7.60 (m, 5H), 9.59-9.83 (brd, 1H). 8-(b)-9  Z 0.92 (t, J =8.0Hz, 3H), 1.23 (d, J = 6.89Hz, 3H), 415 1.42-1.90 (m, 2H), 2.25-2.50(m, 1H), 2.43 (s, 3H), 5.22 (s, 2H), 6.88 (s, 1H), 7.28-7.52 (m, 5H),9.15-9.40 (brd, 1H). 8-(b)-10  Z 1.32 (s, 9H), 2.44 (s, 3H), 5.22 (s,2H), 415 6.88 (s, 1H), 7.28-7.59 (m, 5H), 8.86-9.09 (brd, 1H). 8-(c)-10 Z 1.33 (s, 9H), 2.29 (s, 3H), 5.26 (s, 2H), 6.91 399 (s, 1H), 7.30-7.60(m, 5H), 8.76-8.99 (brd, 1H).

TABLE 76 Compound Table-(a), MS (b), (c)- (m/e, No.   E/Z ¹H-NMR (CDCl₃)δ M⁺) 8-(b)-13  Z 0.89 (t, J = 7.42Hz, 6H), 1.40-1.88 (m, 4H), 4292.04-2.21 (m, 1H), 2.43 (s, 3H), 5.23 (s, 2H), 6.88 (s, 1H), 7.29-7.50(m, 5H), 9.28-9.52 (brd, 1H). 8-(b)-14  Z 2.42 (s, 3H), 5.23 (s, H),7.10 (s, 1H), 427 7.30-7.50 (m, 5H), 8.90-9.20 (brd, 1H). 8-(c)-14  Z2.26 (s, 3H), 5.26 (s, 2H), 7.07 (s, 1H), 411 7.28-7.56 (m, 5H),7.68-8.10 (brd, 1H). 8-(b)-16  Z 2.43 (s, 3H), 5.23 (s, 2H), 7.02 (s,1H), 527 7.29-7.56 (m, 5H). 8-(b)-17  Z 2.44 (s, 3H), 4.27 (s, 2H), 5.24(s, 2H), 6.94 (s, 1H) 407 7.30-7.52 (m, 5H), 9.50-9.75 (brd., 1H).8-(b)-18  Z 2.45 (s, 3H), 5.25 (s, 2H), 6.15 (s, 1H), 6.99 (s, 441 1H),7.30-7.60 (m, 5H), 9.10-10.3 (brd, 1H). 8-(b)-18  E 2.67 (s, 3H), 5.28(s, 2H), 6.16 (s, 1H), 6.99 (s, 1H) 441 7.30-7.60 (m, 5H), 9.10-10.3(brd, 1H). 8-(b)-19  Z 2.45 (s, 3H), 5.24 (s, 2H), 7.03 (s, 1H), 4767.28-7.52 (m, 5H). (M⁺ + 1) 8-(b)-19  E 2.67 (s, 3H), 5.27 (s, 2H), 7.03(s, 1H), 476 7.28-7.52 (m, 5H). (M⁺ + 1) 8-(b)-20  Z 2.06 (s, 6H), 2.45(s, 3H), 5.23 (s, 2H), 6.93 (s, 1H) 479 7.30-7.53 (m, 5H). 8-(b)-20  E2.05 (s, 6H) 2.68 (s, 3H), 5.26 (s, 2H), 6.94 (s, 1H) 479 7.30-7.50 (m,5H). 8-(b)-21  Z 2.44 (s, 3H), 5.25 (s, 2H), 7.15 (s, 1H), 443 7.30-7.56(m, 5H), 10.80-11.15 (brd, 1H). 8-(b)-21  E 2.65 (s, 3H), 5.26 (s, 2H),7.06 (s, 1H), 443 7.29-7.50 (m, 5H).

TABLE 77 Compound Table-(a), MS (b), (c)- (m/e, No.   E/Z ¹H-NMR (CDCl₃)δ M⁺) 8-(b)-22  Z 2.41 (s, 3H), 3.84 (s, 3H), 5.21 (s, 2H), 6.85 (s, 1H)389 7.29-7.50 (m, 5H). 9-(b)-2  Z 2.47 (s, 3H), 2.92 (s, 3H), 5.12 (s,2H), 6.39 (s, 1H) 345 7.30-7.52 (m, 5H). 9-(b)-6  Z 2.41 (s, 3H), 5.02(s, 2H), 6.23 (s, 1H), 6.63 (s, 1H) 574 7.20-7.50 (m, 20H). (M⁺ + 1)9-(c)-6  Z 2.23 (s, 3H), 5.11 (s, 2H), 6.27 (s, 1H), 557 6.80-6.97 (brd,1H), 7.13-7.60 (m, 20H). 9-(b)-7  Z 1.26 (d, J = 6.77Hz, 6H), 2.48 (s,3H), 415 2.93-3.23 (m, 1H), 3.75 (s, 3H), 5.25 (s, 2H), 6.90 (s, 1H),7.30-7.53 (m, 5H). 9-(b)-8  Z 2.15 (s, 3H), 3.07 (s, 6H), 5.14 (s, 2H),6.37 (s, 1H) 359 7.2-7.51 (m, 5H). 9-(b)-9  Z 2.45 (s, 3H), 2.17 (s,3H), 5.13 (s, 2H), 7.04 (s, 1H) 330 7.28-7.55 (m, 5H). 9-(b)-14  Z 2.45(s, 3H), 5.41 (s, 2H), 7.30-7.60 (m, 6H). 384 9-(b)-14  E 2.66 (s, 3H),5.44 (s, 2H), 7.30-7.60 (m, 6H). 384 9-(b)-16  Z 2.44 (s, 3H), 5.34 (s,2H), 7.30-7.52 (m, 5H), 394 8.76 (s, 1H). 9-(b)-16  E 2.67 (s, 3H), 5.36(s, 2H), 7.30-7.50 (m, 5H), 394 8.79 (s, 1H). 9-(b)-20  Z 1.35 (d, J =6.85Hz, 6H), 2.44 (s, 3H), 374 3.95-4.22 (m, 1H), 4.95 (s, 2H), 6.16 (s,1H), 7.30-7.55 (m, 5H). 9-(b)-21  Z 0.88 (d, J = 6.47Hz, 6H), 1.32-1.67(m, 3H), 402 2.42 (s, 3H), 3.50-3.73 (m, 2H), 4.98 (s, 2H), 6.20 (s,1H), 7.30-7.52 (m, 5H).

TABLE 78 Compound Table-(a), (b), (c)- MS No.   E/Z ¹H-NMR (CDCl₃) δ(m/e, M⁺) 9-(b)-22  Z 2.46 (s, 3H), 5.15 (s, 2H), 6.80 (s, 1H), 7.22 414(t, J = 71.7 Hz, 1H), 7.25-7.50 (5H, m). 9-(b)-23  Z 2.46 (s, 3H), 2.67(s, 3H), 5.29 (s, 2H), 7.06 362 (s, 1H), 7.25-7.5 (m, 5H). 9-(b)-26  Z1.40 (d, J = 6.7 Hz, 6H), 2.45 (s, 3H), 3.77 390 (sep, J = 6.7 Hz, 1H),5.30 (d, J = 0.7 Hz, 2H), 7.11 (s, 1H), 7.25-7.5 (m, 5H). 10-(b)-2  Z2.45 (s, 3H), 5.36 (d, J = 0.6 Hz, 2H), 7.23 398 (t, J = 56.5 Hz, 1H),7.25-7.5 (m, 5H). 10-(b)-3  Z 2.46 (s, 3H), 3.30 (s, 3H), 5.41 (s, 2H),7.3-7.5 394 (m, 5H), 7.61 (s, 1H). 10-(b)-4  Z 1.40 (d, J = 6.9 Hz, 6H),2.45 (s, 3H), 3.59 422 (sep, J = 6.9 Hz, 1H), 5.42 (s, 2H), 7.25-7.5 (m,5H), 7.63 (s, 1H). 10-(b)-5  Z 2.43 (s, 3H), 5.40 (s, 2H), 6.45 (t, J =54.4Hz, 414 1H), 7.25-7.5 (m, 5H), 7.68 (s, 1H). 10-(b)-6  Z 2.44 (s,3H), 5.47 (s, 2H), 6.46 (t, J = 53.1Hz, 430 1H), 7.25-7.5 (m, 5H), 7.86(s, 1H). 10-(b)-7  Z 1.27 (d, J = 6.78Hz, 6H), 2.44 (s, 3H), 2.80- 4053.10 (m, 1H), 4.02 (s, 2H), 5.31 (s, 2H), 7.16 (s, 1H), 7.30-7.52 (m,5H). 10-(b)-8  Z 1.41 (t, J = 7.16Hz, 3H), 2.47 (s, 3H), 4.43 388 (q, J= 7.16Hz, 2H), 5.53 (s, 2H), 7.30-7.56 (m, 5H), 8.18 (s, 1H).10-(b)-11  Z 1.27 (d, J = 6.56Hz, 6H), 2.45 (s, 3H), 4.15- 401 4.42 (m,1H), 5.44 (s, 2H), 7.00-7.20 (brd, 1H), 7.30-7.54 (m, 5H) 8.09 (s, 1H).10-(b)-14  Z 2.37 (s, 3H), 2.60 (s, 3H), 3.45 (s, 3H), 5.15 359 (s, 2H),7.11 (s, 1H), 7.25-7.45 (m, 5H). 10-(b)-15  Z 2.39 (s, 3H), 3.37 (s,3H), 3.88 (s, 3H), 5.20 392 (s, 2H), 7.16 (s, 1H), 7.25-7.5 (m, 5H).

TABLE 79 Compound Table-(a), MS (b), (c)- (m/e, No.   E/Z ¹H-NMR (CDCl₃)δ M⁺) 10-(b)-16  Z 2.45 (s, 3H), 2.83 (s, 6H), 5.20 (s, 2H), 7.22 (d, J= 406 1.2 Hz, 1H), 7.3-7.5 (m, 5H), 7.85 (d, J = 1.2 Hz, 1H).10-(b)-20  Z 2.33 (s, 3H), 5.32 (s, 2H), 7.05-7.2 (m, 6H), 7.2- 542 7.5(m, 14H), 7.94 (s, 1H). 11-(b)-1  Z 2.46 (s, 3H), 5.14 (s, 2H), 6.97(brd., 2H), 7.25- 333 7.55 (m, 5H). (M⁺ + 1) 11-(b)-3  Z 2.24 (s, 3H),2.41 (s, 3H), 5.33 (s, 2H), 7.2-7.5 375 (m, 5H). (M⁺ + 1) 11-(b)-7  Z1.25 (d, J = 7.0 Hz, 6H), 2.47 (s, 3H), 2.70 (m, 1H), 403 5.32 (s, 2H),7.25-7.45 (m, 5H). (M⁺ + 1) 11-(b)-10  Z 0.85-1.35 (m), 1.55-2.0 (m),2.39 (d, J = 6.9 Hz, 457 2H), 2.51 (s, 3H), 5.32 (s, 2H), 7.25-7.5 (m,5H). (M⁺ + 1) 11-(b)-11  Z 2.46 (s, 3H), 5.33 (s, 2H), 7.25-7.45 (m,5H). 359 (M⁺ − CF₃) 11-(b)-12  Z 2.45 (s, 3H), 5.18 (s, 2H),7.25-7.45(m, 5H), 7.5- 437 7.6 (m, 2H), 7.6-7.7 (m, 1H), 7.9-8.0 (m,2H). (M⁺ + 1) 11-(b)-13  Z 2.41 (s, 3H), 3.84 (s, 3H), 5.34 (s, 2H),7.2-7.45 391 (m, 5H). (M⁺ + 1) 11-(b)-14  Z 2.48 (s, 3H), 5.19 (s, 2H),7.15-7.5 (m, 20H). 574

TABLE 80 Compound Table-(a), MS (b), (c)- (m/e, No.   E/Z ¹H-NMR (CDCl₃)δ M⁺) 13-(a)-2  Z 1.26 (d, J = 6.8 Hz, 6H), 2.47 (s, 3H), 2.61 (sep, 435J = 6.8 Hz, 1H), 5.25 (s, 2H), 6.90 (s, 1H), 7.25- 7.40 (m, 3H), 7.50(m, 1H). 13-(a)-3  Z 1.27 (d, J = 6.9 Hz, 6H), 2.48 (s, 3H), 2.61 (sep,J = 435 6.9 Hz, 1H), 5.24 (s, 2H), 6.89 (s, 1H), 7.32 (d, J = 8.5 Hz,2H), 7.41 (d, J = 8.5 Hz, 2H), 8.80 (brd, 1H). 13-(b)-3  Z 1.26 (d, J =6.85Hz, 6H), 2.42 (s, 3H), 435 2.50-2.74 (m, 1H), 5.20 (s, 2H), 6.87 (s1H), 7.20-7.45 (m, 4H), 9.08-9.29 (brd, 1H). 13-(a)-8  Z 1.28 (d, J =6.7 Hz, 6H), 2.49 (s, 3H), 2.62 (sep, J = 469 6.7 Hz, 1H), 5.25 (s, 2H),6.90 (s, 1H), 7.29 (dd, J = 2.0, 8.5 Hz, 1H), 7.42 (d, J = 8.5 Hz, 1H),7.60 (d, J = 2.0 Hz, 1H), 8.72 (brd, 1H). 13-(a)-9  Z 1.28 (d, J = 7.1Hz, 6H), 2.49 (s, 3H), 2.62 (sep, J = 469 7.1 Hz, 1H), 5.25 (s, 2H),6.90 (s, 1H), 7.37 (m, 3H), 8.81 (brd, 1H). 13-(b)-12  Z 1.28 (d, J =7.0 Hz, 6H), 2.43 (s, 3H), 2.62 (sep, J = 7.0 Hz, 1H), 5.21 (s, 2H),6.88 (s, 1H), 7.0-7.4 (m, 4H), 8.95 (brd, 1H). 13-(b)-13  Z 2.27 (d, J =6.88Hz, 6H), 2.43 (s, 3H), 419 2.50-2.74 (m, 1H), 5.20 (s, 2H), 6.87 (s,1H). 7.20-7.45 (m, 4H), 9.08-9.29 (brd, 1H). 13-(b)-33  Z 1.26 (d, J =7.0 Hz, 6H), 2.44 (s, 3H), 2.61 (sep, J = 469 7.0 Hz, 1H), 5.25 (s, 2H),6.89 (s, 1H), 7.46 (dd, J = 7.5, 8.1 Hz, 1H), 7.55 (d, J = 8.1 Hz, 1H),7.65 (d, J = 7.5 Hz, 1H), 7.79 (s, 1H), 9.25 brd, 1H).

TABLE 81 Compound Table-(a), MS (b), (c)- (m/e, No.   E/Z ¹H-NMR (CDCl₃)δ M⁺) 23-(b)-12  Z 1.00 (d, J = 6.4 Hz, 6H), 2.1-2.4 (m, 3H), 2.41 (s,433 3H), 5.20 (s, 2H), 6.86 (s, 1H), 7.0-7.4 (m, 4H), 9.9-10.0 (br, 1H).35-(b)-12  Z 2.46 (s, 3H), 4.95 (brd, 2H), 5.11 (s, 2H), 6.43 (s, 3491H), 7.0-7.2 (m, 2H), 7.2-7.4 (m, 2H). 61-(b)-6  Z 2.48 (s, 3H), 5.42(s, 2H), 7.29-7.50 (m, 5H), 7.78 393 (d, J = 6.16Hz, 2H), 8.70 (d, J =6.16Hz, 2H). 61-(b)-14  Z 0.80-1.00 (m, 2H), 1.10-1.23 (m, 2H),1.45-1.70 399 (m, 1H), 2.37 (s, 3H), 5.23 (s, 2H), 6.89 (s, 1H),7.30-7.50 (m, 5H), 10.8-11.0 (brd, 1H). 61-(b)-17  Z 1.12-2.03 (m, 10H),2.20-2.42 (m, 1H), 2.42 (s, 441 3H), 5.22 (s, 2H), 6.87 (s, 1H),7.30-7.50 (m, 5H), 9.10-9.40 (brd, 1H). 61-(b)-19  Z 2.35 (s, 1H), 4.93(s, 2H), 6.90 (s, 1H), 7.30-7.70 436 (m, 8H), 7.85-8.00 (m, 2H).(M⁺ + 1) 63-(b)-20  Z 2.41 (s, 3H), 5.19 (s, 2H), 6.92 (s, 1H), 7.15(dd, 441 J = 3.9, 4.8 Hz, 1H), 7.39-7.50 (m, 5H), 7.64 (d, J = 4.8 Hz,1H) , 7.73 (d, J = 3.9 Hz, 1H). 64-(b)-17  Z 2.40-2.55 (m, 6H),3.90-4.15 (m, 1H), 5.22 (s, 2H), 403 7.29 (s, 1H), 7.40-7.55 (m, 5H).8.20-8.60(m, (M⁺ + 3H)¹⁾. 1) 64-(b)-18  Z 431 (M⁺ + 1) 64-(b)-21  Z1.30-1.60 (m, 3H), 1.48 (s, 9H), 2.43 (s, 3H), 4.20- 503 4.50 (m, 1H),5.20 (s, 2H), 6.88 (s, 1H), 7.30-7.50 (M⁺ + (m, 5H). 1) 64-(b)-22  Z0.94 (d, J = 6.8 Hz, 3H), 1.00 (d, J = 6.8 Hz, 531 3H), 1.45 (s, 9H),2.43 (s, 3H), 4.16-4.40 (m, 1H), (M⁺ + 5.21 (s, 2H), 6.88 (s, 1H),7.30-7.50 (m, 5H). 1) 65-(b)-12  Z 1.11 (d, J = 6.76Hz, 6H), 1.42 (s,9H), 2.44 (s, 3H), 488 4.57 (s, 2H), 5.31 (s, 2H), 7.15 (s, 1H),7.30-7.50 (M⁺ + (m, 5H). 1) ¹⁾Measured in DMSO-d₆

The representations of respective compounds in these tables indicatethat a compound, for example, represented by Compound No. 1-(a)-1 is oneof the compounds shown in Table 1 and Het B of which is type (a).

Hereinafter, examples of formulating agricultural chemicals usingcompounds of oxime derivatives obtained by present invention will bedescribed. Unless otherwise shown, the compounds are mixtures of the “Z”and the “E” forms.

FORMULATING EXAMPLE 1

Dust powder

2 parts by weight of the oxime derivatives from Compound No. 1-(a)-1 toCompound No. 66-(b)-10 were mixed with 98 parts by weight of clay andthe mixture was pulverized so that dusting powder was produced.

FORMULATING EXAMPLE 2

Water-dispersible powder

20 parts by weight of the oxime derivatives from Compound No. 1-(a)-1 toCompound No. 66-(b)-10 were mixed with 68 parts by weight of clay, 8parts by weight of white carbon, and 4 parts by weight ofpolyoxyethylenenonylphenylether and the mixture was pulverized so thatwater-dispersible powder was produced.

FORMULATION EXAMPLE 3

Granular

5 parts by weight of the oxime derivatives from Compound No. 1-(a)-1 toCompound No. 66-(b)-10 were mixed with 90 parts by weight of a mixtureof equivalent weights of bentonite and talc and 5 parts by weight ofsodium alkylbenzenesulfonate and the mixture was pulverized for forminggranules.

The effectiveness of the compounds obtained by the present inventionagainst various plant diseases will be hereinafter described withreference to following test examples. The status of the test plants atthe time of testing the control effects of the present chemicals, thatis, the degree of lesions appearing on foliage or the number of plantsattacked by Phytophthora are visually observed, and the results wereevaluated by four grades “A”, “B”, “C”, and “D”. Grade “A” was selectedwhen there is no plant with lesions or no withered plant, and grade “B”was selected when the number of diseased plants, which include plantswith lesions or withered plants, is around 10% among the total numbersof plants. Grade “C” was selected when the number of diseased plant isaround 25%, and grade “D” was selected when the diseased plants exceed50%.

TEST EXAMPLE 1 Control Test of Plant Disease Caused by Phytophthorainfestans

The water-dipersable powder prepared by the method shown in FormulationExample 2 was diluted with water containing a surface active agent(0.02%) so as to contain the effective component at a concentration of250 ppm. The thus prepared solution was sprayed on foliage at the 3 to 4leaf stage of tomatoes (variety: Toyofuku) which were grown in plasticpots with a diameter of 9 cm. After drying in air, a dispersion ofspores of Phytophthora infestans was spray-inoculated and, afterstanding in a wet room at 20° C. for 24hours, the spores were made growat room temperature. After 5 days, the degree of disease was determined.The test results in terms of Phytophthora infestans of tomato are shownin Table 82. Water dispersible powder of manzeb in amounts of 1,250 ppmand 250 ppm was used as a reference agricultural chemical.

TABLE 82 Compound number Evaluation 1-(a)-1 A 1-(b)-9 B 4-(a)-3 B4-(a)-13 A 4-(b)-13 B 4-(a)-22 B 4-(a)-33 A 6-(a)-18 B 6-(a)-19 B6-(b)-19 B 8-(a)-1 B 8-(b)-4 B 8-(a)-7 A 8-(b)-7 A 8-(c)-7 A 8-(b)-8 B8-(b)-9 B 8-(b)-10 B 8-(b)-14 B 13-(a)-2 A Reference chemical 1250 ppm A 250 ppm C

TEST EXAMPLE 2 Control Test of Plant Disease Caused by Pseudoperonosporacubensis

The water-dipersable powder prepared by the method shown in FormulationExample 2 was diluted with water containing a surface active agent(0.02%) so as to contain the effective component at a concentration of50 ppm. The thus prepared solution was sprayed on foliage at the 3 leafstage of a cucumber (variety: Tokiwa Shinchibai) which was grown in aplastic pot with a diameter of 9 cm. After drying in air, a dispersionof spores of Pseudoperonospora cubensis was spray-inoculated and, afterstanding in a wet room at 25° C. for 24hours, the spores were made growat room temperature. After 5 days, the degree of disease was determined.The test results in terms of Pseudoperonospora cubensis of cucumber areshown in Table 83. Water dispersible powder of manzeb in amounts of1,250 ppm and 50 ppm was used as a reference agricultural chemical.

TABLE 83 Compound number Evaluation 1-(a)-1 A 1-(b)-1 A 6-(a)-18 A8-(a)-1 B 8-(b)-3 A 8-(b)-7 A 8-(c)-7 A 8-(b)-9 A 8-(b)-10 A 8-(b)-14 B13-(a)-2 B 13-(b)-13 A Reference chemical 1250 ppm A  50 ppm D

TEST EXAMPLE 3 Control Test of Plant Disease Caused by Pseudoperonosporacubensis (Leaf disc test)

The first leaf of a cucumber (variety: Tokiwa Shinchibai) at a 2 to 3leaf stage was stamped into a disc with a diameter of 10 mm. The discwas then immersed for 30 minutes in a solution of a pharmaceuticalchemical at an effective ingredient concentration of 10 ppm using awater-dispersible powder prepared according to the Formulating Example2. After drying in air, a dispersion of spores of Pseudoperonosporacubensis (a metalaxyl resistant fungi strain) was drop-inoculated.Standing in a wet room, the bacteria was cultured in an artificialweathering equipment (14 hours a day, 2° C. in a day, 18° C. at night)for 7 days, and the degree of the disease was determined. The testresult of this leaf test in relation to Pseudoperonospora cubensis isshown in Table 84. A 10 ppm of the water-dispersible powder of manzeband that of metalaxyl was used as the reference agricultural chemical.

TABLE 84 Compound Reference number Evaluation chemical Evaluation1-(a)-1 A Manzeb C 8-(b)-1 A Metalaxyl D 8-(b)-3 A 8-(b)-4 A 8-(b)-7 A8-(b)-8 A 8-(b)-9 A 8-(b)-13 A 8-(b)-18 B 9-(b)-16 A 9-(b)-22 B 9-(b)-23A 9-(b)-26 A 10-(b)-2 B 10-(b)-5 B 13-(a)-2 A 13-(b)-3 A 13-(b)-12 A13-(b)-13 A 13-(b)-33 A 61-(b)-6 A 61-(b)-14 A 61-(b)-19 A 63-(b)-20 B

TEST EXAMPLE 4 Control Test of Plant Disease Caused by Plasmoparaviticola (leaf disc test)

A leaf disc formed by stamping a leaf of an alley grown vine (variety:neo masukatto) was immersed in a chemical-containing solution which wasprepared using a water-dispersible powder at an effective componentconcentration of 10 ppm for 30 min. After drying in air, a dispersion ofspores of two fungi consisting of (A) metalaxyl-sensitive Plasmoparaviticola and (B) metalaxyl-resistant Plasmopara viticola wasdrop-inoculated, and the fungi was cultured for seven days in a wet roomby an artificial weathering instrument. The test result of this leaftest in relation to Plasmopara viticola was shown in Table 85.

TABLE 85 Evaluation Compound Metalaxyl-sensitive Metalaxyl-resistantnumber Plasmopara viticola A Plasmopara viticola B 8-(b)-4 A A 8-(b)-4 AA 8-(b)-4 A A 8-(b)-10 A A 8-(b)-13 B B 61-(b)-14 B B 61-(b)-19 A AReference chemical Manzeb C C Metalaxyl A D

TEST EXAMPLE 5 Control Test of a Plant Disease Caused by Pythiumaphanidermatum

A mixture of sterilized soil and Pythium aphanidermatum was put in adeep petri-dish with a diameter of 15 cm. After seeding 10 seeds ofcucumber (variety: Nouryoku Shintokiwa) for each pot, a water-diluteddispersion of water-dispersible powder prepared according to theFormulating Example 2 at the effective component concentration of 1,000ppm was drenched on the soil. After drenched, the pot was placed in awet room and was subjected to a weathering instrument with a day-lengthof 14 hours for 4 days. The degree of the plant disease was determined.The test result in relation to Pythium aphanidermatum was shown in Table86. The reference agricultural chemical of this test was 1,000 ppm of awater-dispersible powder of captan.

TABLE 86 Compound number Evaluation 1-(a)-1 A 8-(b)-7 A 8-(b)-10 AReference B chemical

TEST EXAMPLE 6 Control Test of a Plant Disease Caused by Pyriculariaoryzae

A water diluted solution of a water-dispersible powder preparedaccording to Formulating Example 2 at an effective componentconcentration of 250 ppm was sprayed on foliage of a rice plant(variety: Aichi Asahi) at a 3 to 4 leaf stage which was grown in aplastic pot with a diameter of 9 cm. After drying in air, a dispersionof spores of Pyricularia oryzae was spray-inoculated, and after standingin a wet room for 24 hours, the plant disease was developed in a glasshouse, and the degree of the plant disease was determined after 7 days.The test result in relation to Pyricularia oryzae was shown in Table 87.The reference agricultural chemical of this test was 500 ppm of awater-dispersible powder of phthalide.

TABLE 87 Compound number Evaluation 1-(a)-1 A 1-(a)-9 A 1-(b)-9 A4-(a)-3 A 4-(a)-13 A 4-(a)-22 B 6-(a)-18 A 6-(b)-18 A 6-(a)-19 B6-(b)-19 B Reference chemical 500 ppm A 250 ppm B

Furthermore, the practical structures of compounds of the presentinvention are shown in Table 88 to 90, wherein Het B, Het C, X, Y, and nare the same as those defined in the general formulas (1) and (2), andMe represents a methyl group.

TABLE 88

No Xn 1 2-Cl 2 3-Cl 3 4-Cl 4 2,3-(Cl)₂ 5 2,4-(Cl)₂ 6 2,5-(Cl)₂ 72,6(Cl)₂ 8 3,4-(Cl)₂ 9 3,5-(Cl)₂ 10 2,4,6-(Cl)₃ 11 2-F 12 3-F 13 4-F 142,3-(F)₂ 15 2,4-(F)₂ 16 2,5-(F)₂ 17 2,6-(F)₂ 18 3,4-(F)₂ 19 3,5-(F)₂ 202,4,6-(F)₃ 21 2-CH₃ 22 3-CH₃ 23 4-CH₃ 24 2,3-(CH₃)₂ 25 2,4-(CH₃)₂ 262,5-(CH₃)₂ 27 2,6-(CH₃)₂ 28 3,5-(CH₃)₂ 29 3-Cl,5-CH₃ 30 3-F,5-CH₃ 313-F,5-Cl 32 2-CF₃ 33 3-CF₃ 34 4-CF₃ 35 2-CN 36 3-CN 37 4-CN 38 2-SMe 393-SMe 40 4-SMe 41 2-SO₂Me 42 3-SO₂Me 43 4-SO₂Me 44 2-Br 45 3-Br 46 4-Br47 2-OH 48 3-OH 49 4-OH 50 2-OMe 51 3-OMe 52 4-OMe

TABLE 89

No Het —C Xn 1

H 2

H 3

H 4

H 5

H 6

H 7

H 8

H 9

H 10

H 11

H 12

H 13

H 14

H 15

H 16

H

TABLE 90

No Het —C Xn 1

3-F 2

4-F 3

H 4

H 5

H 6

H 7

H 8

H 9

H 10

H 11

H 12

H 13

H 14

H 15

H 16

H 17

H 18

H 19

H 20

H 21

H 22

H 23

H 24

H 25

H 26

3-F

Physical chemical data such as ¹H-NMR spectra and mass spectra of oximederivatives prepared by the same methods as those shown in ManufacturingExample 1 to 9 are shown in Tables 91 to 97.

TABLE 91 Com- pound Table-(a), MS (b), (c)- (m/e, No.      E/Z ¹H-NMR(CDCl₃) δ M+) 4-(c)-2   Z 2.32 (s, 3H), 5.41 (s, 2H), 7.12-7.48 (m, 5H),328 7.53-7.62 (m, 1H), 7.70 (t, J = 7.69Hz, 1H), 8.59 (d, J = 4.S3Hz,1H). 4-(c)-3   Z 2.32 (s, 3H), 5.40 (s, 2H), 7.11-7.41 (m, 4H), 328 7.48(d, J = 8.69Hz, 2H), 7.69 (t, 7.63Hz, 1H), 8.58 (d, J = 4.64Hz, 1H).4-(c)-12  Z 2.32 (s, 3H), 5.41 (s, 2H), 6.98-7.48 (m, 6H), 312 7.70 (t,J = 7.63Hz, 1H), 8.59 (d, J = 4.81Hz, 1H). 4-(c)-13  Z 2.33 (s, 3H),5.40 (s, 2H), 6.98-7.13 (m, 2H), 312 7.14-7.36 (m, 2H), 7.45-7.63 (m,2H), 7.69 (t, J = 7.75Hz, 1H), 8.58 (d, J = 4.63Hz, 1H). 4-(c)-33  Z2.34 (s, 3H), 5.44 (s, 2H), 7.16-7.35 (m, 2H), 362 7.41-7.58 (m, 1H),7.61-7.82 (m,3H), 7.87 (s, 1H), 8.60 (d, J = 4,69z, 1H). 8-(b)-5   Z1.00 (t, J = 7.37Hz, 3H), 1.61-1.90 (m, 2H), 401 2.28-2.54 (m, 2H), 2.43(s, 3H), 5.22 (s, 2H), 6.87 (s, 1H), 7.28-7.51 (m, 5H), 8.95-9.23 (brd,1H). 8-(b)-6   Z 0.39 (t, J = 7.6Hz, 3H), 1.30-1.49 (m, 2H), 1.62- 1.79(m, 2H), 2.42 (t, J = 7.6Hz, 2H), 2.42 (s, 3H), 415 5.21 (s, 2H), 6.87(s, 1H), 7.30-7.46 (m, 5H), 9.18- 9.36 (brd, 1H). 8-(b)-11  Z 1.07 (s,9H), 2.30 (s, 2H), 2.40 (s, 3H), 5.21 (s, 429 2H), 6.87 (s, 1H),7.25-7.5 (m, 5H), 7.8-8.2 (brd, 1H). 8-(b)-23  Z 1.33 (t, J = 7.09Hz,3H), 2.39 (s, 3H), 4.28 403 (q, J = 7.14Hz, 2H), 5.25 (s, 2H), 6.83 (s,1H), 7.28-7.50 (m, 5H). 8-(b)-24  Z 1.32 (t, J = 6.22Hz, 6H), 2.40 (s,3H), 4.95-5.19 417 (m, 1H), 5.24 (s, 2H), 6.81 (s, 1H), 7.30-7.52 (m,5H). 13-(b)-2  Z 1.28(d, J = 7.0Hz, 6H), 2.43(s, 3H), 2.61(seq, J = 4357.0Hz, 1H), 5.22(s, 2H), 6.87(s, 1H), 7.2-7.5(m, 4H), 8.79(brd, 1H).13-(b)-22  Z 1.28(d, J = 7.0Hz, 6H), 2.33(s, 3H), 2.43(s, 3H), 2.61(seq,J = 7.0Hz, 1H), 5.21(s, 2H), 6.86(s, 1H), 7.15-7.4(m, 4H), 8.78(brd,1H). 13-(b)-23  Z 1.27(d, J = 7.0Hz, 6H), 2.35(s, 3H), 2.43(s, 3H),2.61(seq, J = 7.0Hz, 1H), 5.20(s, 2H), 6.86(s, 1H), 7.14(d, J = 8.0Hz,2H), 7.31 (d, J = 8.0Hz, 2H), 8.80(brd, 1H). 13-(b)-45  Z 1.28(d, J =6.8Hz, 6H), 2.43(s, 3H), 2.59(seq, J = 479 6.8Hz, 1H), 5.22(s, 2H),6.88(s, 1H), 7.20(dd, J = 7.8, 7.8Hz, 1H), 7.29(d, J = 7.8Hz, 1H),7.52(d, J = 7.8Hz, 1H), 7.66(s, 1H), 8.74(brd, 1H).

TABLE 92 Com- pound Table-(a), MS (b), (c)- (m/e, No.      E/Z ¹H-NMR(CDCl₃) δ M+) 13-(b)-46  Z 1.28(d, J = 6.8Hz, 6H), 2.43(s, 3H), 2.61(seq, J = 479 6.8Hz, 1H), 5.21(s, 2H), 6.87(s, 1H), 7.30(m, 2H), 7.48(m,2H), 8.71(brd, 1H). 13-(b)-52  Z 1.26(d, J = 5.3Hz, 6H), 2.42(s, 3H),2.58(seq, J = 5.3Hz, 1H), 3.81(s, 3H), 5.18(s, 2H), 6.85(m, 3H), 7.35(m,2H), 9.11(brd, 1H). 13-(c)-2  Z 1.28 (d,J = 6.88Hz, 6H), 2.28 (s, 3H),2.45-2.76 419 (m, 1H), 5.26 (s, 2H), 6.91 (s, 1H), 7.26-7.48 (m, 3H),7.53-7.69 (m,1H), 8.70-8.91 (brd, 1H). 13-(c)-3  Z 1.28 (d, J = 6.96Hz,6H), 2.28 (s, 3H), 2.50-2.75 419 (m, 1H), 5.24 (s, 2H), 6.91 (s, 1H),7.34 (d, J = 8.67 Hz, 2H), 7.48 (d, J = 8.73Hz, 2H), 8.63-8.85 (brd,1H). 13-(c)-12  Z 1.28 (d, J = 6.94Hz, 6H), 2.29 (s, 3H), 2.49-2.74 403(m, 1H), 5.25 (s, 2H), 6.91 (s, 1H), 7.04-7.45 (m, 4H), 8.78 (s, 1H).13-(c)-13  Z 1.28 (d, J = 6.94Hz, 6H), 2.29 (s, 3H), 2.48-2.78 403 (m,1H), 5.24 (s, 2H), 6.90 (s, 1H), 7.07 (t, J = 8.90 Hz, 2H), 7.45-7.53(m, 2H), 8.63-8.90 (brd, 1H). 13-(c)-33  Z 1.27 (d, J = 6.93Hz, 6H),2.29 (s, 3H), 2.47-2.77 453 (m, 1H), 5.28 (s, 2H), 6.93 (s, 1H),7.39-7.60 (m, 1H), 7.61-7.78 (m, 2H), 7.68 (s, 1H), 9.20 (s, 1H).17-(c)-13  Z 1.50-2.10 (m, 8H), 2.29 (s, 3H), 2.70-2.92 429 (m, 1H),5.23 (s, 2H), 6.89 (s, 1H), 7.00-7.12 (m, 2H), 7.51-7.62 (m, 2H),8.71-8.92 (brs, 1H) 23-(a)-2  Z 0.99 (d, J = 6.4Hz, 3H), 2.0-2.4 (m,1H), 2.47 (s, 449 3H), 5.25 (s, 2H), 6.90 (s, 1H), 7.25-7.45 (m, 4H),9.29 (brd, 1H). 23-(b)-2  Z 1.01 (d, J = 6.2Hz, 6H), 2.22(m, 1H),2.30(d, J = 449 6.4Hz, 2H), 2.43(s, 3H), 5.22(s, 2H), 6.87(s, 1H),7.2-7.5(m, 4H), 8.80(brd, 1H). 23-(b)-12  Z 1.00(d, J = 6.4Hz, 6H),2.1-2.4(m, 3H), 2.41(s, 433 3h), 5.20(s, 2H), 6.86(s, 1H), 7.0-7.4(m,4H), 9.94 (brd, 1H). 23-(b)-45  Z 1.01(d, J = 6.6Hz, 6H), 2.21(m, 1H),2.30(d, J = 493 6.4Hz, 2H), 2.43(s, 3H), 5.22(s, 2H), 6.87(s, 1H),7.20(dd, J = 7.9, 7.9Hz, 1H), 7.30(m, 1H), 7.52(m, 1H), 7.66(dd, J =1.8, 1.8Hz, 1H), 8.89(brd, 1H). 23-(b)-46  Z 1.01(d, J = 6.4Hz, 6H),2.21 (m, 1H), 2.30(d, J = 493 6.4Hz, 2H), 2.42(s, 3H), 5.20(s, 2H),6.86(s, 1H), 7.30(m, 2H), 7.47(m, 2H), 8.76(brd, 1H).

TABLE 93 Com- pound Table-(a), MS (b), (c)- (m/e, No.      E/Z ¹H-NMR(CDCl₃) δ M+) 23-(c)-2  Z 1.01 (d, J = 6.33Hz, 6H), 2.10-2.44 (m, 3H),2.28 433 (s, 3H), 5.26 (s, 2H), 6.91 (s, 1H), 7.18-7.48 (m, 3H), 7.61(s, 1H), 8.95 (s, 1H). 23-(c)-3  Z 0.99 (d, J = 6.43Hz, 6H), 2.13-2.38(m, 3H), 2.26 433 (s, 3H), 5.24 (s, 2H), 6.90 (s, 1H), 7.33 (d, J =8.78Hz, 2H), 7.47 (d, J = 8.71Hz, 2H), 9.30 (s, 1H). 23-(c)-12  Z 0.99(d, J = 6.36Hz, 6H), 2.08-2.50 (m, 3H), 2.27 417 (s, 3H), 5.26 (s, 2H),6.91 (s, 1H), 7.05-7.47 (m, 4H), 9.11-9.38 (brd, 1H). 23-(c)-13  Z 1.00(d, J = 6,23Hz, 6H), 2.07-2.45 (m, 3H), 2.28 417 (s, 3H), 5.24 (s, 2H),6.90 (s, 1H), 6.96-7.18 (m, 2H), 7.42-7.68 (m, 2H), 8.82-9.14 (brd, 1H).37-(b)-45  Z 2.43(s, 3H), 5.24(s, 2H), 6.94(s, 1H), 7.15-7.35(m, 5132H), 7.5-7.7(m, 5H), 7.9-7.95(m, 1H), 9.5(brd, 1H). 37-(b)-46  Z 2.41(s, 3H), 5.16 (s, 2H), 6.93 (s, 1H), 7.25-7.35 513 (m, 2H), 7.45-7.55(m, 4H), 7.55-7.70 (m, 1H), 7.90-7.95 (m, 2H), 9.77 (brd, 1H). 61-(b)-16 Z 1.46-2.02 (m, 8H), 2.42 (s, 3H), 2.65-2.91 (m,1H), 427 5.21 (s, 2H),6.86 (s, 1H), 7.28-7.53 (m, 5H), 9.03-9.28 (brd, 1H). 61-(b)-20  Z 2.41(s, 3H), 5.16 (s, 2H), 6.94 (s, 1H), 7.28-7.48 469 (m, 5H), 7.49 (d, J =8.63Hz, 2H), 7.91 (d, J = 8.59Hz, 2H). 61-(b)-21  Z 2.44 (s, 3H), 5.23(s, 2H), 6.95 (s, 1H), 7.30-7.66 471 (m, 7H), 7.75-7.88 (m, 1H), 7.98(s, 1H). (M⁺ + 1) 61-(b)-22  Z 2.45 (s, 3H), 5.21 (s, 2H), 6.95 (s, 1H),7.31-7.60 469 (m, 8H), 7.91 (d, J = 6.59Hz,l H). 61-(b)-23  Z 2.44 (s,3H), 5.21 (s, 2H), 6.96 (s, 1H), 7.30-7.47 503 (m, 5H), 7.52 (d, J =1.95Hz, 1H), 7.87(d, J = 8.43Hz, 1H). 62-(b)-3  Z 2.43 (s, 3H), 5.22 (s,2H), 6.94 (s, 1H), 7.12-7.28 453 (m, 2H), 7.30-7.50 (m, 5H), 7.88-8.09(m, 2H). 62-(b)-11  Z 2.39 (s, 3H), 2.42 (s, 3H), 5.08 (s, 2H), 6.90 (s,449 1H), 7.25-7.50 (m, 7H), 7.80 (d, J = 8.23Hz, 2H). 62-(b)-20  Z 2.42(s, 3H), 5.20 (s, 2H), 6.97 (s, 1H), 7.30-7.53 503 (m, 5H), 7.79 (d, J =8.28Hz, 2H), 8.07 (d, J = 8.13Hz, 2H).

TABLE 94 Com- pound Table-(a), MS (b), (c)- (m/e, No.      E/Z ¹H-NMR(CDCl₃) δ M+) 62-(b)-21  Z 2.36 (s, 3H), 5.01 (s, 2H), 6.95 (s, 1H),7.29-7.47 503 (m, 5H), 7.63 (t1 J = 7.82Hz, 1H), 7.84 (d, J =7.83Hz,1H), 8.10 (d, J = 7.92Hz, 1H), 8.23 (s, 1H). 62-(b)-17  Z 2.27(s, 6H), 2.36 (s, 3H), 4.70 (s, 2H), 6.87 (s, 464 1H), 7.03 (d, J =7.77Hz, 2H), 7.10-7.45 (m, 6H). (M⁺ + 1) 62-(b)-23  Z 2.38 (s, 3H), 3.86(s, 3H), 5.06 (s, 2H), 6.89 (s, 465 1H), 6.96 (d, J = 8.93Hz, 2H),7.30-7.50 (m, 5H), 7.88 (d, J = 8.93Hz, 2H), 10.20-10.70 (brd, 1H).62-(b)-24  Z 2.46 (s, 3H), 4.09 (s, 3H), 5.27 (s, 2H), 6.91 (s, 1H) 4657.06 (d, J = 8.40Hz, 1H), 7.15 (t, J = 7.58Hz, 1H), 7.29-7.50 (m, 5H),7.56 (t, J = 6.96Hz, 1H), 8.30 (d, J = 7.84Hz, 1H), 11.06 (s, 1H).62-(b)-26  Z 2.40 (s, 3H), 4.13 (brd, 2H), 5.12 (s, 2H), 6.67 (d, 450 J= 10.0Hz, 2H), 6.87 (s, 1H), 7.28-7.43 (m, 5H), 7.74 (d, J = 10.0Hz,2H), 9.95-10.36 (brd, 1H). 63-(b)-5  Z 2.39 (s, 3H), 5.11 (s, 2H), 6.97(s, 1H), 7.29-7.50 460 (m, 5H), 7.80 (d, J = 8.41Hz, 2H), 8.04 (d, J =8.40Hz, 2H). 64-(b)-14  Z 2.39 (s, 3H), 3.79 (s, 2H), 5.16 (s, 2H), 4496.86 (s, 1H), 7.29-7.50 (m, 10H). 65-(b)-4  Z 1.26 (d, J = 6.50Hz, 6H),2.41 (s, 3H), 3.22-3.50 388 (m, 1H), 4.41-4.66 (m, 2H), 5.34 (s, 2H),7.28-7.60 (M⁺ + (m, 5H), 7.83 (s, 1H), 9.20-9.46 (brd, 1H). 1) 88-(b)-2 Z 1.32 (s, 9H), 2.43 (s, 3H), 5.22 (s, 2H), 6.87 (s, 449 1H), 7.2-7.5(m, 4H), 9.05 (brd, 1H). 88-(b)-3  Z 1.32 (s, 9H), 2.42 (s, 3H), 5.20(s, 2H), 6.87 (s, 449 1H), 7.20-7.45 (m, 4H), 9.35 (brd, 1H). 88-(c)-3 Z 1.33 (s, 9H), 2.29 (s, 3H), 5.25 (s, 2H), 6.91 (s, 433 1H), 7.35 (d,J = 8.84Hz, 2H), 7.49 (d, J = 8.84Hz, 2H), 8.84 (s,1H). 88-(b)-12  Z1.32 (s, 9H), 2.42 (s, 3H), 5.21 (s, 2H), 6.88 (s, 433 1H), 7.0-7.4 (m,4H), 9.55 (brd, 1H). 88-(c)-12  Z 1.33 (s, 9H), 2.29 (s, 3H), 5.26 (s,2H), 6.91 (s, 417 1H), 6.99-7.16 (m, 2H), 7.43-7.69 (m, 2H), 8.72- 9.00(brd, 1H). 88-(b)-13  Z 1.32 (s, 9H), 2.43 (s, 3H), 5.20 (s, 2H), 6.87(s, 433 1H), 7.2-7.45 (m, 4H), 9.30 (brd, 1H). 88-(c)-13  Z 1.33 (s,9H), 2.30 (s, 3H), 5.24 (s, 2H), 6.91 (s, 417 1H), 6.99-7.16 (m, 2H),7.43-7.69 (m, 2H), 8.72- 9.00 (brd, 1H).

TABLE 95 Com- pound Table-(a), MS (b), (c)- (m/e, No.      E/Z ¹H-NMR(CDCl₃) δ M+) 88-(b)-22  Z 1.32(s, 9H), 2.33(s, 3H), 2.44(s, 3H),5.22(s, 2H), 6.87(s, 1H), 7.15-7.4(m, 4H), 8.83(brd, 1H). 88-(b)-23  Z1.32(s, 9H), 2.35(s, 3H), 2.43(s, 3H), 5.20(s, 2H), 6.86(s, 1H), 7.15(d,J = 8.0Hz, 2H), 7.31 (d, J = 8.0Hz, 2H), 8.86(brd, 1H). 88-(b)-52  Z1.32(s, 9H), 2.44(s, 3H), 3.81(s, 3H), 5.19(s, 2H), 6.86(m, 3H), 7.36(m,2H), 8.86(brd, 1H). 89-(b)-5  Z 1.60-2.05 (m, 8H), 2.39 (s, 3H),2.70-2.97 (m, 1H), 428 5.30 (s, 2H), 7.30-7.57 (m, 6H). (M⁺ + 1)89-(b)-6  Z 2.40 (s, 3H), 5.30 (s, 2H), 7.19 (s, 1H), 7.30-7.60 470 (m,7H), 7.93 (d, J = 8.61Hz, 2H). (M⁺ + 1) 89-(b)-7  Z 2.39 (s, 3H), 4.72(s, 2H), 5.32 (s, 2H), 6.86-7.14 466 (m, 3H), 7.24-7.58 (m, 8H).(M⁺ + 1) 89-(b)-8  Z 2.42 (s, 3H), 5.17 (s, 2H), 5.38-5.83 (brd, 2H),375 6.71 (s, 1H), 7.30-7.52 (m, 5H). (M⁺ + 1) 89-(b)-12  Z 2.42 (s, 3H),3.04 (s, 6H), 5.18 (s, 2H), 6.77 (s, 403 1H), 7.28-7.52 (m, 5H).(M⁺ + 1) 89-(b)-13  Z 1.06-2.01 (m, 10H), 2.41 (s, 3H), 3.53-3.88 (m,457 1H), 5.19 (s, 2H), 6.69 (s, 1H), 7.27-7.51 (m, 5H). (M⁺ + 1)89-(b)-14  Z 2.41 (s, 3H), 5.23 (s, 2H), 6.78 (s, 1H), 7.04-7.53 451 (m,10H). (M⁺ + 1) 89-(b)-15  Z 1.20 (d, J = 6.54Hz, 6H), 2.41 (s, 3H),3.84-4.10 416 (m, 1H), 5.18 (s, 2H), 6.69 (s, 1h), 7.29-7.52 (m, 5H).90-(c)-1  Z 2.27 (s, 9H), 4.72 (s, 2H), 5.29 (s, 2H), 6.80-7.40 468 (m,10H), 9.80 (s, 1H). (M⁺ + 1) 90-(c)-2  Z 2.28 (s, 9H), 4.72 (s, 2H),5.27 (s, 2H), 6.806-7.00 467 (m, 3H), 7.00-7.15 (m, 3H), 7.28-7.42 (m,2H), 7.43-7.64 (m, 2H), 9.76 (s, 1H). 90-(b)-3  Z 2.44 (s, 3H), 4.72 (s,2H), 5.25 (s, 2H), 465 6.98-7.17 (m, 4H), 7.30-7.54 (m, 7H). 90-(c)-3  Z2.26 (s, 3H), 4.70 (s, 2H), 5.27 (s, 2H), 449 6.72-7.69 (m, 10H), 6.95(s, 1H), 9.86 (s, 1H). 90-(b)-6  Z 1.44 (s, 6H), 2.48 (s, 3H), 3.71 (s,2H), 5.22 (s, 2H) 449 6.89 (s, 1H), 7.28-7.56 (m, 5H). 90-(b)-9  Z 1.33(s, 6H), 2.45 (s, 3H), 2.81 (s, 2H), 5.23 (s, 2H) 461 6.88 (s, 1H),7.29-7.52 (m, 5H), 9.20-9.48 (brd, 1H)

TABLE 96 Com- pound Table-(a), MS (b), (c)- (m/e, No.      E/Z ¹H-NMR(CDCl₃) δ M+) 90-(b)-10  Z 1.57(s, 6H), 2.45(s, 3H), 2.95(s, 3H),3.50(s, 2H), 493 5.23(s, 2H), 6.90(s, 1H), 7.28-7.52(m, 5H), 9.00-9.23(brd, 1H). 90-(b)-12  Z 0.93 (d, J = 6.48Hz, 6H), 1.96-2.19 (m, 1H),2.38 432 (s, 3H), 4.01 (d, J = 6.81Hz, 2H), 5.26 (s, 2H), 6.82 (M⁺ + (s,1H), 7.28-7.51 (m, 5H). 1) 90-(b)-13  Z 2.30 (s, 3H), 5.32 (s, 2H), 6.90(s, 1H), 7.06-7.20 451 (m, 2H), 7.21-7.48 (m, 8H). 90-(b)-14  Z 1.98 (s,3H), 2.33 (s, 3H), 4.77 (d, J = 5.95Hz, 2H), 416 5.27 (s, 2H), 6.88 (s,1H), 7.20-7.48 (m, 5H), 11.15-11.55(brd, 1H). 90-(b)-15  Z 1.27(d, J =6.9Hz, 6H), 2.44(s, 3H), 2.60(seq, J = 6.9Hz, 1H), 5.18(s, 2H),7.25-7.45(m, 5H), 8.68(brd, 1H). 90-(b)-16  Z 0.79-1.01 (m, 3H),1.28-1.45 (m, 2H), 1.70-1.86 429 (m, 2H), 2.30-2.55 (m, 2H), 2.43 (s,3H), 5.21 (s, (brd, 1H). 90-(b)-17  Z 2.43 (s, 3H), 3.87 (s, 3H), 5.20(s, 2H), 6.93 (s, 465 1H), 7.08-7.20 (m, 1H), 7.29-7.54 (m, 8H), 9.56-9.96 (brd, 1H). 90-(b)-18  Z 2.50 (s, 3H), 5.43 (s, 2H), 7.22 (s, 1H),7.30-7.50 460 (m, 5H), 7.80-7.89 (m, 2H), 7.98-8.03 (m, 2H).

TABLE 97 Com- pound Table-(a), MS (b), (c)- (m/e, No.      E/Z ¹H-NMR(CDCl₃) δ M+) 1-(b)-12  Z 2.50 (s, 3H), 5.32 (s, 2H), 7.15-7.26 (m, 2H),7.30- 345 7.50 (m, 5H), 7.64 (t, J = 7.77Hz, 1H). 1-(c)-12  Z 2.35 (s,3H), 5.36 (s, 2H), 7.12-7.30 (m, 2H), 7.32- 329 7.57 (m, 5H), 7.66 (t, J= 7.80Hz, 1H). 7-(b)-15  Z 2.41 (s, 3H), 5.07 (s, 2H), 7.02 (s, 1H),7.32-7.53 332 (m, 5H), 8.93 (s, 2H). (M⁺ + 1) 7-(b)-16  Z 1.29 (d, J =6.93Hz, 6H), 2.39 (s, 3H), 2.56-2.77 402 (m, 1H), 5.30 (s, 2H),7.31-7.56 (m, 6H). (M⁺ + 1) 7-(b)-17  Z 1.33 (s, 9H), 2.39 (s, 9H), 5.30(s, 2H), 7.30-7.55 416 (m, 6H). (M⁺ + 1) 7-(b)-18  Z 2.39 (s, 3H), 5.31(s, 2H), 7.30-7.55 (m, 6H), 360 8.57 (s, 1H). (M⁺ + 1) 90-(b)-19  Z 1.92(dd, J = 1.5, 7.0Hz, 3H), 2.40 (s, 3H), 5.22 (s, 399 2H), 5.96 (dd, J =1.5, 15Hz, 1H), 7.11 (dq, J = 15, 7.0Hz, 1H), 7.2-7.5 (m, 5H), 9.5-10.0(brd, 1H). 90-(b)-20  Z 1.90 (d, J = 1.0Hz, 3H), 2.26 (d, J = 1.0Hz,3H), 413 2.41 (s, 3H), 5.23 (s, 2H), 5.69 (t, J = 1.0Hz, 1H), 6.86 (s,1H), 7.2-7.5 (m, 5H), 10.1 (brd, 1H).

Furthermore, test examples of pesticides according to the presentinvention will be described hereinafter.

TEST EXAMPLE 7 Control Test of a Plant Disease Caused byPseudoperonospora cubensis

A control test was executed by the same method as that shown in TestExample 2. The test result is shown in Table 98.

TABLE 98 Compound number Evaluation  4-(c)-12 A  4-(a)-13 A  4-(b)-13 A 4-(c)-13 A  7-(a)-10 A  8-(c)-8 A  8-(c)-10 A 13-(a)-8 B 13-(b)-12 A13-(c)-13 A 61-(b)-14 B 61-(b)-16 A 61-(b)-20 A 90-(b)-3 A

TEST EXAMPLE 8 Control Test of a Plant Disease Caused byPseudoperonospora cubensis (Leaf disc test)

A control test was executed by the same method as that shown in TestExample 3. The test result is shown in Table 99.

TABLE 99 Compound number Evaluation  1-(c)-1 A  2-(a)-1 A  4-(c)-3 B 4-(c)-12 A  4-(a)-13 A  4-(b)-13 A  4-(c)-13 A  8-(c)-7 A  8-(c)-8 A 8-(b)-10 A  8-(c)-10 A  8-(b)-24 A 13-(b)-2 A 13-(a)-3 A 13-(a)-8 A13-(c)-13 A 23-(a)-2 A 61-(b)-16 A 61-(b)-20 A 64-(b)-14 A 64-(b)-22 A90-(b)-3 A 90-(b)-19 A

TEST EXAMPLE 9 Control Test of a Plant Disease Caused by Plasmoparaviticola (Leaf disc test)

A control test was executed by the same method as that shown in TestExample 4. The test result is shown in Table 100.

TABLE 100 Compound Compound number Evaluation number Evaluation  1-(b)-9B 13-(c)-12 B  1-(c)-9 B 13-(b)-13 A  4-(a)-2 B 13-(c)-13 A  4-(c)-2 B13-(b)-22 B  4-(c)-12 A 13-(b)-23 B  4-(c)-13 A 13-(b)-45 B  4-(c)-33 B23-(a)-2 A  6-(b)-19 B 23-(b)-2 A  8-(b)-5 A 23-(c)-12 B  8-(c)-7 A23-(c)-13 B  8-(c)-8 A 23-(b)-45 B  8-(b)-9 A 61-(b)-16 A  8-(c)-10 A61-(b)-20 A  8-(b)-11 B 62-(b)-24 A  8-(b)-17 B 63-(b)-5 A  8-(b)-24 A64-(b)-14 A 13-(a)-2 A 88-(c)-13 A 13-(b)-2 A 88-(b)-22 A 13-(c)-2 B89-(b)-12 B 13-(a)-3 B 90-(c)-1 A 13-(b)-3 A 90-(c)-2 B 13-(a)-8 A90-(c)-3 A 13-(b)-12 A 90-(b)-15 B

INDUSTRIAL APPLICABILITY

The present invention provides novel oxime derivatives, which do notcause any chemical damage to plants and have sufficient effectivenessagainst various plant diseases, and also provides pesticides and controlagents to remove plant diseases which contain those oxime derivatives asactive ingredients.

What is claimed is:
 1. An oxime derivative expressed by the followinggeneral chemical formula (1),

wherein, R¹ represents a hydrogen atom or a lower alkyl group; Xrepresents a halogen atom, a nitro group, a hydroxyl group, a cyanogroup, a carboxyl group, an alkoxy-carbonyl group, a lower alkyl groupwhich may be substituted with halogen atoms; a lower alkoxy group whichmay be substituted with halogen atoms; a lower alkylthio group which maybe substituted with halogen atoms; a lower alkylsulfonyl group which maybe substituted with a halogen atom; an aryl group which may besubstituted with a halogen atom or a lower alkyl group; an aryloxy groupwhich may be substituted with a halogen atom or a lower alkyl group; oran amino group which may be substituted with a lower alkyl group; and nrepresents an integer from 0 to 3; and Het A represents a 6-memberedaromatic nitrogen-containing ring which contains one or two nitrogenatoms or its benzo-condensation ring-type nitrogen containing aromaticring which may be substituted with one or two substitutable groupsselected from the group consisting of a halogen atom, a lower alkylgroup, a lower alkylthio group, a lower alkylsulfonyl group, a loweralkoxy group, a trifluoromethyl group, and a cyano group; and Het Brepresents oxime derivatives, each ring structure, expressed by thefollowing formulas,

wherein, Y represents a hydrogen atom, a halogen atom, or a lower alkylgroup which may be substituted with a halogen atom.
 2. An oximederivative expressed by the following general formula (2)

wherein, R¹ ,X, n, Het B, and Y are the same as those defined in thechemical formula (1), and Het C represents a 5-membered nitrogencontaining aromatic ring or its benzo-condensation ring-type nitrogencontaining aromatic ring which contains more than one nitrogen atom, orwhich may contain a sulfur atom or an oxygen atom, and which may besubstituted with more than one substituting group, and the substitutablegroups on a nitrogen atom of said 5-membered nitrogen containingaromatic ring are groups selected from the group consisting of a loweralkyl group, a lower alkyl-sulfonyl group, triphenylmethyl group, alower alkoxymethyl group and a N, N-di-substituted sulfamoyl groupsubstituted with lower alkyl groups, and the substitutable groups on acarbon atom of said 5 membered nitrogen containing aromatic ring aregroups selected from the group consisting of a halogen atom, a cyanogroup, an alkyl group ranging from C₁ to C₆ which may be substitutedwith a halogen atom, and a cycloalkyl group ranging from C₃ to C₆; andan alkenyl group ranging from C₂ to C₆, an alkinyl group ranging from C₂to C₆, an alkoxy group ranging from C₁ to C₅ which may be substitutedwith a halogen atom, a lower alkylthio group which may be substitutedwith a halogen atom, a lower alkylsulfonyl group which may besubstituted with a halogen atom, a lower alkyl sulfinyl group which maybe substituted with halogen atoms, an amino group which may besubstituted with a lower alkyl group or a cycloalkyl group ranging fromC₃ to C₆ or a triphenyl-methyl group; and a lower alkoxy-carbonyl group,a carbamoyl group which may be substituted with lower alkyl groups, anaminomethyl group which may be substituted with lower alkyl groups, anacylaminomethyl group, N-alkoxycarbonyl-aminomethyl group, an alkylthiomethyl group, aryl group which may be substituted with halogenatoms, and a heteroaryl group which may be substituted with halogenatoms, and a group expressed by —N (R²) C (═O) R³ (wherein, R²represents a hydrogen atom or a methyl group, and R³ represents ahydrogen atom, an alkyl group ranging from C₁ to C₁₀ which may besubstituted with halogen atoms, a cycloalkyl group ranging from C₃ toC₈, an alkenyl group ranging from C₂ to C₆, an alkinyl atoms rangingfrom C₂ to C₄, an aralkyl group, a lower alkyl group substituted with anamino group, an aralkyl group substituted with an amino group, a loweralkyl group substituted with an acylamino group, an aralkyl groupsubstituted with an acylamino group, a lower alkyl group substitutedwith an alkoxy-carbonyl-amino group, an aralkyl group substituted withan alkoxy-carbonyl-amino group, an aryl group which may be substitutedwith halogen atoms, lower alkyl groups which may be substituted withhalogen atoms, lower alkoxy groups, lower alkylthio groups, aminogroups, nitro groups or cyano groups, a heteroaryl group, a lower alkoxygroup, a cycloalkyloxy group ranging from C₃ to C₆, a benzyloxy groupand an aryloxy group).
 3. An oxime derivatives according to claim 1,wherein Het A in the general formula (1) is a pyridyl group which may besubstituted with a halogen atom or a lower alkyl group.
 4. An oximedeivative according to claim 2, wherein Het C in the general formula (2)is expressed by the following formula

wherein, R⁴ represents a hydrogen atom, an amino group, an alkoxy groupranging from C₁ to C₅ which may be substituted with halogen atoms, alower alkylthio group which may be substituted with halogen atoms, alower alkylsulfonyl group which may be substituted with halogen atoms, alower alkylsulfinyl group which may be substituted with halogen atoms;or a —NHC (═O) R³ group (wherein, R³ represents a hydrogen atom, analkyl group ranging from C₁ to C₁₀ which may be substituted with halogenatoms, a cycloalkyl group ranging from C₃ to C₈, an alkenyl groupranging from C₂ to C₆, an alkinyl group ranging from C₂ to C₄, anaralkyl group, a lower alkyl group substituted with an amino group, anaralkyl group substituted with an amino group, a lower alkyl groupsubstituted with an acylamino group, an aralkyl group substituted withan acyl-amino group, a lower alkyl group substituted with analkoxycarbonylamino group, an aralkyl group substituted with analkoxycarbonylamino group; an aryl group which may be substituted withhalogen atoms, lower alkyl groups which may be substituted with halogenatoms, lower alkoxy groups, lower alkylthio groups, amino groups, nitrogroups, or cyano groups; a heteroaryl group, a lower alkoxy group, or acycloalkyloxy group ranging from C₃ to C₆, a benzyl oxy group, or aaryloxy group); and R⁵ represents a hydrogen atom, a halogen atom, or alower alkyl group which may be substituted with a halogen atom.
 5. Anoxime derivative according to claim 4, wherein R⁴ is a group expressedby —NHC (═O) R³ (wherein, R³ represents a hydrogen atom, an alkyl groupranging from C₁ to C₆ which may be substituted with halogen atoms, alower cycloalkyl group ranging from C₃ to C₆, an aryl group which may besubstituted with halogen atoms, lower alkyl groups which may besubstituted with halogen atoms, lower alkoxy groups, amino groups, orcyano groups; a heteroaryl group, or a lower alkoxy group), and R⁵ is ahydrogen atom.
 6. A pesticide containing oxime derivatives according toclaims 1 to 5 as active ingredient.
 7. A plant disease control agentwhich contains at least one of the oxime derivatives according to claims1 to 5 as active ingredient.
 8. A plant disease control agent accordingto claim 7, which is effective for plant diseases caused by mold fungi.9. A method of manufacturing a hydroxyimino compound expressed by thefollowing general chemical formula (b):

wherein X, n, and Het B are as defined for the following generalchemical formula (a), the method comprising the step of reacting anazole-methanone compound expressed by the following general chemicalformula (a) with a hydroxylamine:

wherein X represents a halogen atom, a nitro group, a hydroxyl group, acyano group, a carboxyl group, an alkoxy-carbonyl group, a lower alkylgroup which may be substituted with halogen atoms; a lower alkoxy groupwhich may be substituted with halogen atoms; a lower alkylthio groupwhich may be substituted with halogen atoms; a lower alkylsulfonyl groupwhich may be substituted with a halogen atom; an aryl group which may besubstituted with a halogen atom or a lower alkyl group; an aryloxy groupwhich may be substituted with a halogen atom or a lower alkyl group; oran amino group which may be substituted with a lower alkyl group; and nrepresents an integer from 0 to 3; and Het B represents oximederviatives, each ring structure, expressed by the following formulas,

wherein, Y represents a hydrogen atom, a halogen atom, or a lower alkylgroup which may be substituted with a halogen atom.
 10. A method ofmanufacturing an oxime derivative expressed by the following generalchemical formula (1) or (2): general chemical formula (1):

wherein Het B, X, and n are as defined for the following generalchemical formula (b), and Het A and R¹ are as defined for the followinggeneral chemical formula (c) general chemical formula (2):

wherein Het B, X, and n are as defined for the following generalchemical formula (b), and Het C and R¹ are as defined for the followinggeneral chemical formula (d), the method comprising the step of reactinga hydroxyimino compound expressed by the following general chemicalformula (b) with a halogen compound expressed by the following generalchemical formula (c) or (d) in the presence of a base: general chemicalformula (b):

wherein X represents a halogen atom, a nitro group, a hydroxyl group, acyano group, a carboxyl group, an alkoxy-carbonyl group, a lower alkylgroup which may be substituted with halogen atoms; a lower alkoxy groupwhich may be substituted with halogen atoms; a lower alkylthio groupwhich may be substituted with halogen atoms; a lower alkylsulfonyl groupwhich may be substituted with a halogen atom; an aryl group which may besubstituted with a halogen atom or a lower alkyl group; an aryloxy groupwhich may be substituted with a halogen atom or a lower alkyl group; oran amino group which may be substituted with a lower alkyl group; and nrepresents an integer from 0 to 3; and Het B represents oximederivatives, each ring structure, expressed by the following formulas,

wherein, Y represents a hydrogen atom, a halogen atom, or a lower alkylgroup which may be substituted with a halogen atom, general chemicalformula (c):

wherein, R¹ represents a hydrogen atom or a lower alkyl group; Het Arepresents a 6-membered aromatic nitrogen-containing ring which containsone or two nitrogen atoms or its benzo-condensation ring-type nitrogencontaining aromatic ring which may be substituted with one or twosubstitutable groups selected from the group consisting of a halogenatom, a lower alkyl group, a lower alkylthio group, a loweralkylsulfonyl group, a lower alkoxy group, a trifluoromethyl group, anda cyano group; and Z represents a chlorine atom, a bromine atom, or aniodine atom, general chemical formula (d)

wherein, R¹ represents a hydrogen atom or a lower alkyl group; Het Crepresents a 5-membered nitrogen containing aromatic ring or itsbenzo-condensation ring-type nitrogen containing aromatic ring whichcontains more than one nitrogen atom, or which may contain a sulfur atomor an oxygen atom, and which may be substituted with more than onesubstituting group, and the substitutable groups on a nitrogen atom ofsaid 5-membered nitrogen containing aromatic ring are groups selectedfrom the group consisting of a lower alkyl group, a lower alkyl-sulfonylgroup, triphenylmethyl group, a lower alkoxymethyl group and a N,N-di-substituted sulfamoyl group substituted with lower alkyl groups,and the substitutable groups on a carbon atom of said 5 memberednitrogen containing aromatic ring are groups selected from the groupconsisting of a halogen atom, a cyano group, an alkyl group ranging fromC₁ to C₆ which may be substituted with a halogen atom, and a cycloalkylgroup ranging from C₃ to C₆; and an alkenyl group ranging from C₂ to C₆,an alkinyl group ranging from C₂ to C₆, an alkoxy group ranging from C₁to C₅ which may be substituted with a halogen atom, a lower alkylthiogroup which may be substituted with a halogen atom, a loweralkylsulfonyl group which may be substituted with a halogen atom, alower alkyl sulfinyl group which may be substituted with halogen atoms,an amino group which may be substituted with a lower alkyl group or acycloalkyl group or a cycloalkyl group ranging from C₃ to C₆ or atriphenyl-methyl group; and a lower alkoxy-carbonyl group, a carbamoylgroup which may be substituted with lower alkyl groups, an aminomethylgroup which may be substituted with lower alkyl groups, anacylaminomethyl group, N-alkoxycarbonyl-aminomethyl group, an alkylthiomethyl group, aryl group which may be substituted with halogenatoms, and a heteroaryl group which may be substituted with halogenatoms, and a group expressed by —N(R²) C(═O) R³ (wherein, R² representsa hydrogen atom or a methyl group, and R³ represents a hydrogen atom, analkyl group ranging from C₁ to C₁₀ which may be substituted with halogenatoms, a cycloalkyl group ranging from C₃ to C₈, an alkenyl groupranging from C₂ to C₆, an alkinyl group ranging from C₂ to C₄, anaralkyl group, a lower alkyl group substituted with an amino group, anaralkyl group substituted with an amino group, a lower alkyl groupsubstituted with an acylamino group, an aralkyl group substituted withan acylamino group, a lower alkyl group substituted with analkoxy-carbonyl-amino group, an aralkyl group substituted with analkoxy-carbonyl-amino group, an aryl group which may be substituted withhalogen atoms, lower alkyl groups which may be substituted with halogenatoms, lower alkoxy groups, lower alkylthio groups, amino groups, nitrogroups or cyano groups, a heteroaryl group, a lower alkoxy group, acycloalkyloxy group ranging from C₃ to C₆, a benzyloxy group and anaryloxy group); and Z represents a chlorine atom, a bromine atom, or aniodine atom.
 11. A hydroxyimino compound of the following generalchemical formula (b):

wherein X represents a halogen atom, a nitro group, a hydroxyl group, acyano group, a carboxyl group, an alkoxy-carbonyl group, a lower alkylgroup which may be substituted with halogen atoms; a lower alkoxy groupwhich may be substituted with halogen atoms; a lower alkylthio groupwhich may be substituted with halogen atoms; a lower alkylsulfonyl groupwhich may be substituted with a halogen atom; an aryl group which may besubstituted with a halogen atom or a lower alkyl group; an aryloxy groupwhich may be substituted with a halogen atom or a lower alkyl group; oran amino group which may be substituted with a lower alkyl group; and nrepresents an integer from 0 to 3; and Het B represents oximederivatives, each ring structure, expressed by the following formulas,

wherein, Y represents a hydrogen atom, a halogen atom, or a lower alkylgroup which may be substituted with a halogen atom.
 12. A hydroxyiminocompound according to claim 11, wherein in the general chemical formula(b), X represents a halogen atom; a lower alkyl group which may besubstituted with halogen atoms; a lower alkoxy group which may besubstituted with halogen atoms; or an aryl group; and n represents 0 to3.
 13. A hydroxyimino compound according to claim 11, wherein in thegeneral chemical formula (b), X represents a lower alkyl group rangingfrom C₁ to C₂, a fluoroalkyl group ranging from C₁ to C₂, or a halogenatom; and n represents 0 to
 3. 14. A hydroxyimino compound according toclaim 11, wherein in the general chemical formula (b), n is 0, and Y inHet B is a methyl group.